Do I sell it all and call it a day??

Multi-Family and Apartment Investing
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Do I sell it all and call it a day??

Stephen Jones
Rental Property Investor · IL · Member since 2019 · 285 posts · 137 votes

BP,

I've been wrestling back and forth on whether or not I should sell my entire multifamily portfolio and get out of the game, so I figured I'd throw a post on here to get a little insight!

My current portfolio consists of 160 multifamily apartment units, over the course of a 10 year period it has taken a lot of hard work and sacrifice to get to the point of where I am. 

Most of my portfolio is mainly B class properties, with some A class properties mixed in. All in decent/good locations. All properties have been managed very well over the years and currently has a great tenant base with no vacancies.

The main reason of potentially wanting to sell is that the maintenance calls are starting to wear on me. I manage all these properties by myself and it just takes a toll dealing with 160 people on a daily basis. I've went down the road with a management company before, and I refuse to go back down that road. It is what it is, other people don't manage or treat the properties like the actual owner. It is essentially, my baby. 

I am also only 37 years old. Which I'd like to think is still a fairly young man lol. So do I hang on for 5 more years or so? I still do enjoy the game of chasing deals, it is what really keeps me going and gets me excited, but managing after the fact has just turned to wearing on me a bit. 

Also, most of my property is based in Illinois (it is my backyard) and the taxes around here are brutal. It's just not the best state to be invested in, as I'm sure you all know. 

I would absolutely miss the cash flow aspect of it though, getting re occurring income every month is definitely something I weigh in not to sell. 

I would prefer not to go into numbers on here, but if it comes down to it, I will. If inboxing me is better to get into the numbers game, feel free to do so!

I know that is all fairly brief, so if there's any other questions, feel free to ask! I appreciate all the feedback!




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Andrew FreedBusiness Member
Investor · Worcester, MA · Member since 2020 · 1k+ posts · 1k+ votes
1y

@Stephen Jones - I truly think your issue is you are not utilizing leverage and delegation effectively. You can build an entire property management company pennies on the dollar if you hire internationally and yes, it will take from your profit, but it will buy you back time. I recommend reading Buy Back your Time, amazing book and all fundamentals you should be utilizing given the size of your portfolio. I personally think if you hold and learn how to leverage others, hire right and delegate effectively, you will be much happier and richer in the long run. I personally own over 400 doors and have done this across my portfolio so I'm talking from experience. Feel free to reach out if you want some best practices. 

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  • Andrew FreedBusiness Member
    Investor · Worcester, MA · Member since 2020 · 1k+ posts · 1k+ votes
    1y

    @Stephen Jones - I truly think your issue is you are not utilizing leverage and delegation effectively. You can build an entire property management company pennies on the dollar if you hire internationally and yes, it will take from your profit, but it will buy you back time. I recommend reading Buy Back your Time, amazing book and all fundamentals you should be utilizing given the size of your portfolio. I personally think if you hold and learn how to leverage others, hire right and delegate effectively, you will be much happier and richer in the long run. I personally own over 400 doors and have done this across my portfolio so I'm talking from experience. Feel free to reach out if you want some best practices. 

    [email protected]781-964-3200Podcast Guest on Show 69 Doors from ONE Real Estate Deal Using Other People’s Money
    11Reply
  • Stephen Jones
    OP
    Rental Property Investor · IL · Member since 2019 · 285 posts · 137 votes
    1y

    @Andrew Freed- Great advice. Thanks for the message and congrats on the 400 doors! That's saying something man!

    2Reply
  • Dave Charron
    Investor · Syracuse, NY · Member since 2010 · 166 posts · 76 votes
    1y

    I agree with Andrew, your definitely at the point financially where you could hire a maintenance guy to cover service calls, turnovers and regular upgrades to the properties.  For admin help you could get part time if needed.

    This should take some of that stress off your table.

    4Reply
  • Theresa HarrisPro Member
    Member since 2019 · 15k+ posts · 11k+ votes
    1y

    Why not get a handyman to help with the service calls (doesn't have to be full time, but as on call basis)...or a couple you can rely on?  You have a lot of properties, so sit down and figure out which ones are more problematic, will have upcoming large expenses (eg new roof in 2-5 years) and aren't performing well.  Also if you sell, you should have some cash from the sale that you can invest elsewhere.

    3Reply
  • Ken M.
    Investor · Get yourself trained before doing something inadvisable. · Member since 2024 · 3k+ posts · 1k+ votes
    1y
    Quote from @Stephen Jones:

    BP,

    I've been wrestling back and forth on whether or not I should sell my entire multifamily portfolio and get out of the game, so I figured I'd throw a post on here to get a little insight!

    My current portfolio consists of 160 multifamily apartment units, over the course of a 10 year period it has taken a lot of hard work and sacrifice to get to the point of where I am. 

    Most of my portfolio is mainly B class properties, with some A class properties mixed in. All in decent/good locations. All properties have been managed very well over the years and currently has a great tenant base with no vacancies.

    The main reason of potentially wanting to sell is that the maintenance calls are starting to wear on me. I manage all these properties by myself and it just takes a toll dealing with 160 people on a daily basis. I've went down the road with a management company before, and I refuse to go back down that road. It is what it is, other people don't manage or treat the properties like the actual owner. It is essentially, my baby. 

    I am also only 37 years old. Which I'd like to think is still a fairly young man lol. So do I hang on for 5 more years or so? I still do enjoy the game of chasing deals, it is what really keeps me going and gets me excited, but managing after the fact has just turned to wearing on me a bit. 

    Also, most of my property is based in Illinois (it is my backyard) and the taxes around here are brutal. It's just not the best state to be invested in, as I'm sure you all know. 

    I would absolutely miss the cash flow aspect of it though, getting re occurring income every month is definitely something I weigh in not to sell. 

    I would prefer not to go into numbers on here, but if it comes down to it, I will. If inboxing me is better to get into the numbers game, feel free to do so!

    I know that is all fairly brief, so if there's any other questions, feel free to ask! I appreciate all the feedback!




    Done properly, 160 Units should throw off a pretty good income AND a FULL TIME handyman. Look over your numbers and figure out what you're doing wrong.
    9Reply
  • Jay HinrichsBusiness Member
    Real Estate Consultant · Summerlin, NV · Member since 2014 · 45k+ posts · 66k+ votes
    1y

    Look at net cash out after tax.. then use 4 to 6% income on that sum minus income tax and see where that puts you.. if its more than enough to live your life raise your family if you have one then well why not.. my self I ramped up to 300 SFRs and hated it .. sold out did not make a ton but moved that into renting my cash for income. I like that a lot .. plus building new homes has been very nice and having the cash I got from selling the homes allowed me the liquidity to get horizontal and vertical construction loans..  Just one way to do it. With out dealing with tenants. which to me resi tenants is well something I dont really like.

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    3Reply
  • Chris Howell
    Tulsa ok · Member since 2025 · 84 posts · 60 votes
    1y

    Definitely Agree with Andrew. Its time to hire a maintenance man and a manager. Spend 6 months teaching them your system and automate the repair request that go straight to your handyman and keep your phone from ringing. This still keeps you active and in the business with the parts of investing you love and you can still keep everything running the way you want. Spend the money to take the 160 headaches away. You will just have 1 to 2 headaches to deal with. Congratulations on 160 Doors. I am in process of trying to switch from SFR to multi family.

    2Reply
  • Jamie O'Connell
    Rental Property Investor · Elmira NY · Member since 2023 · 143 posts · 143 votes
    1y

    I would say you've worked so hard to build it up and I assume it's a great margin that you should hold on. I would say if you make a good amount I would go about hiring a specific person to do what you do. So if your making 20k a month in profit (just an assumption but using for a point) spend 5 - 7 k or something a month and hire someone full time to do what you do so your making 13k a month but its 13k a month that is truly "passive". 

    Still a very solid income. You know your numbers better than anyone but thats what I did. I hired someone who handles everything and just comes to me when it's something big aka we need to evict or need a new roof etc etc. so while I make less a month, I do nothing for that income. 

    4Reply
    • Demario Scott
      New to Real Estate · Belleville, IL · Member since 2018 · 82 posts · 42 votes
      1y

      @Jamie O'Connell I'm not there yet, but interesting. I would figure the vetting process would be extensive, but could certainly make it very passive.

      0Reply
    • Jamie O'Connell
      Rental Property Investor · Elmira NY · Member since 2023 · 143 posts · 143 votes
      1y
      Quote from @Demario Scott:

      @Jamie O'Connell I'm not there yet, but interesting. I would figure the vetting process would be extensive, but could certainly make it very passive.


       Yes I am lucky I knew someone in the town (I am out of state most of the time) who is a people person, smart and also handy enough to do small little things like toilets, trying small fixes before calling in professional etc. So you definitely need someone who can work on their own so it takes a bit to find normally but definitely worth it. 

      0Reply
  • Edward Branagan
    Investor · Clayton, NC · Member since 2025 · 1 post · 0 votes
    1y

    I have a 14 unit Apartment building  under contract per $1,800,000.The property is in Benson, NC. I’m wholesaling $1,900,000 the closing date is July 14, 2025

    0Reply
    • Art Webb
      Member since 2019 · 50 posts · 7 votes
      1y
      Quote from @Edward Branagan:

      I have a 14 unit Apartment building  under contract per $1,800,000.The property is in Benson, NC. I’m wholesaling $1,900,000 the closing date is July 14, 2025


       Curious, what kind of real estate commission and closing costs are you paying for that $100K difference ?

      0Reply
  • Melissa ThompsonPro Member
    Member since 2025 · 3 posts · 1 vote
    1y

    Selfishly I wish I was in your shoes....i think you should hang in there, take advice from those who have been there before. Good luck! 

    1Reply
  • Alecia LovelessPro Member
    Member since 2019 · 3k+ posts · 2k+ votes
    1y

    @Stephen Jones I have a portfolio 1/5 the size of yours but have a handyman to deal with the maintenance issues. This frees me up to do the parts I enjoy including leasing, tenant relations and buying new deals.

    I strongly recommend you figure out how to focus more on the parts you enjoy and spend less time on the parts that you’re “over”.

    Yes, your cash flow will be affected if you hire someone to help, but if it allows you to stay in the game another 5-10 years or indefinitely you will reap the benefits of mortgage pay down and appreciation.

    1Reply
  • Demario Scott
    New to Real Estate · Belleville, IL · Member since 2018 · 82 posts · 42 votes
    1y

    I'm located in the Southern Illinois area and me and my brother are very handy. I'm well versed with horizontal construction and he is more vertical HVAC, renovations and such. We are both actively searching to be more involved in the real estate realm and would certainly be able to help with tenant request or even finding solid contractors.

    1Reply
  • Ryan Randall
    NH · Member since 2016 · 56 posts · 73 votes
    1y

    I'll be on the other side and say yes, you should sell. Peace of mind can be priceless. If it feels right, go for it.

    0Reply
  • Kate Sanchez
    Member since 2025 · 248 posts · 101 votes
    1y

    @Stephen Jones  Totally get it - 160 units solo is no joke. Maybe selling part & reinvesting passively could ease burnout while keeping cash flow. You’ve built something incredible!

    0Reply
  • Keith Jablonowski
    Property Manager · Lombard, IL · Member since 2013 · 100 posts · 82 votes
    1y

    The tax consequences alone of just straight up selling should scare you away from that idea. If you do decide to sell, make sure to explore 1031 exchange into a DST (Delaware Statutory Trust). You will defer your tax hit and keep a lot of your cash flow with 0 stress.

    3Reply
  • Patricia DeVane
    Member since 2025 · 1 post · 4 votes
    1y

    First off, kudos. Managing 160 units solo over a decade is no small feat, and the fact that your portfolio is stable, well-tenanted, and in good condition speaks volumes about your discipline and commitment.

    It sounds like you’re at a true crossroads, not just with your portfolio, but personally too. The burnout from hands-on management is real, especially when you feel the weight of maintaining something you’ve poured yourself into. Wanting to step back doesn’t mean failure, it might just mean it’s time to evolve your strategy.

    A few things to chew on:

    • Could you offload some units rather than all? Trimming the portfolio might reduce your stress without severing your connection to the game or cash flow.
    • What about building a small, loyal in-house team? Not quite a management company, but maybe a trusted assistant or maintenance lead you can train your way. You’d still have control, just not all the chaos.
    • Geographic diversification? Illinois taxes are brutal, no doubt. Maybe this is a chance to pivot toward friendlier markets while still staying in real estate. This I could help you with in NC, by introducing you great realtors who specialize in investment property.
    • And lastly, if deal-making is what lights your fire, how could you focus your energy more on acquisitions or partnerships and less on day-to-day operations?


    You’re young, seasoned, and clearly still passionate. Maybe it’s not about walking away, it’s about shifting how you play. The game’s not over; maybe it’s just time for a different position on the court.

    Appreciate you sharing this, whatever you decide, you’ve earned the right to choose it from a place of power.

    4Reply
  • George SkidisPro Member
    Rental Property Investor · Belleville, IL · Member since 2017 · 875 posts · 529 votes
    1y

    First issue. If you sell a unit, you will pay capital gains tax. The calculation is basis Sales Price - (Purchase price + Repairs and Renovations - Accumulated depreciation) = Capital Gains. So, imagine you purchased and rehabbed a unit, and today you have $200,000 in it. But you have owned it about 13 years and have taken $100,000 in depreciation on your taxes reducing your basis in the property to $100,000. 

    Example: You are selling at $275K so 275K - 100K depreciated basis = capital gains of $175,000.  If you are in a 20% tax bracket that gives you a tax bill of $35,000 for that unit. Can you afford to do that 100+ times? Do you have any accumulated tax losses you can use against this gain?

    Getting in is always easier than getting out. 

    So now it is time to get a list of contractors and handymen to lift some of your burden. An when you sell only one building at a time. Start with your least profitable.

    1Reply
  • Don KonipolBusiness Member
    Investor · The Woodlands TX / Avon, CT · Member since 2009 · 6k+ posts · 10k+ votes
    1y
    Quote from @Stephen Jones:

    BP,

    I've been wrestling back and forth on whether or not I should sell my entire multifamily portfolio and get out of the game, so I figured I'd throw a post on here to get a little insight!

    My current portfolio consists of 160 multifamily apartment units, over the course of a 10 year period it has taken a lot of hard work and sacrifice to get to the point of where I am. 

    Most of my portfolio is mainly B class properties, with some A class properties mixed in. All in decent/good locations. All properties have been managed very well over the years and currently has a great tenant base with no vacancies.

    The main reason of potentially wanting to sell is that the maintenance calls are starting to wear on me. I manage all these properties by myself and it just takes a toll dealing with 160 people on a daily basis. I've went down the road with a management company before, and I refuse to go back down that road. It is what it is, other people don't manage or treat the properties like the actual owner. It is essentially, my baby. 

    I am also only 37 years old. Which I'd like to think is still a fairly young man lol. So do I hang on for 5 more years or so? I still do enjoy the game of chasing deals, it is what really keeps me going and gets me excited, but managing after the fact has just turned to wearing on me a bit. 

    Also, most of my property is based in Illinois (it is my backyard) and the taxes around here are brutal. It's just not the best state to be invested in, as I'm sure you all know. 

    I would absolutely miss the cash flow aspect of it though, getting re occurring income every month is definitely something I weigh in not to sell. 

    I would prefer not to go into numbers on here, but if it comes down to it, I will. If inboxing me is better to get into the numbers game, feel free to do so!

    I know that is all fairly brief, so if there's any other questions, feel free to ask! I appreciate all the feedback!




    Lots of REALLY GOOD posts here in response.  However, my take is a little different.  You hate to delegate, because other people don’t care as much as you, don’t do as good a job as you, do it less efficiently than you, are not as motivated as you, and won’t produce the optimum results that you will.  It doesn’t matter whether or not these beliefs are correct, the fact that YOU believe them is what’s driving your methods. 

    So, you essentially have three choices. First, you can continue as is and at best continue to have that feeling of being “trapped”, at worst “burn out”.  Second, as you suggest you can sell and say goodbye to ACTIVE real estate investing.  Or third (what I did) is you can remain as an ACTIVE real estate investor in a way that doesn’t require intensive management or reliance on other people to manage your business.  I did it through (1) hard money/private mortgage lending and note purchases and (2) triple net leased properties (in my case to non credit tenants for yields double what credit tenants would bring).  Here’s the thing - $10 million invested in apartments with yourself as manager is a full time 60 hours + a week job with constant “fires” to be put out.  $10 million commercial mortgage notes is 5 - 10 notes with monthly payments ACH into your account and spending maybe 3 hours per week IF you “service” your own loans. ( Finding or originating the loans IS time consuming but it’s not management and it FUN!). Similarly $10 million could cover 5 - 10 3N properties with the with tenants responsible for taxes, insurance AND maintenance.  

    Bottom line is you can scale BIG without having to manage long hours or intensive management, nor having to “delegate”. 

     
    Let me know if I’m anywhere close to target with my response. 

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    3Reply
  • James Hamling
    Real Estate Broker · Minneapolis, MN · Member since 2011 · 5k+ posts · 6k+ votes
    1y

    @Stephen Jones there is a lot more to it than just the money, and I fear all too many responders are going to miss that. 

    Yes, in theory you could start on the journey of people leverage, hiring staff, focusing energy to hiring, training, managing, and the unfortunate reality of firing and doing it all over again. 

    But that isn't for everyone, people miss that. Anyone can cook, being a Chef isn't for anyone. Just because one can doesn't mean they will be happy at it. 

    You said a few things that has me thinking you'd maybe be much happier exiting the life and time consumption of Landlording, and being free to focus on deal making. 

    Well how about this.... 

    You have achieved a level most never get close to. What if you go back and diary how you did it all, and knowing what you know now, how you'd do it if you had it to do all over again with this decade wiser. 

    And then, go ahead, sell, stack up the capitol, and formulate your knowledge into a program, and launch a community, program, cult, whatever. 

    In this you can do 2 things simultaneously. 

    (A) Helping so many people via real, actual "this is how I DID it" knowledge. Of course compensating for your knowledge, yes that holds a value, but it really would help people. 

    (B) Now you can focus your time and energies on the thing you really like, the deal making. Because with the "group" you can present a potential JV into deals, but also just being the knowledgeable eyes looking at the deals that group brings and advising for the various how-to.

    I say life is too short to do what everyone thinks you should do vs perusing your passions. 

    Miss the reoccurring revenue, well there ya go, charge $10mnth. 

    The #1 reason so many of us detest the "Guru's" is not for being a Guru, it's because so many are over selling, over charging, and under delivering. They are selling hope and false promises.      For the legit few, I applaud them. 

    2Reply
  • Ezekiel Trevino
    Realtor · McAllen, TX · Member since 2025 · 141 posts · 58 votes
    1y

    It all depends on your financial goal. How much money do you want make? Will you have enough money for retirement after taxes? If you have kids, have you set some money aside for them if they decide to pursure a college degree or fund their first real estate investment? 

    I understand that refuse to go back to hiring a property manager. There are some property managers that are good at managing and taking care of your investment while others are in it for the money. In my opinion looking for a property manager is a hit or miss. I hate to say it, but you gotta suck it up and deal with the maintenance calls. Do you do the repairs yourself or hire a handyman? If you have a handyman do the repairs and get a lot of maintenance calls, I'd start looking for a another handyman. 

    In my opinion, hang on to those properties and keep building your portfolio. Build some generational wealth. Teach your kids (if you have any) about real estate investing. That way when they are older and understand real estate investing, you can pass on your portfolio and have them build more gernational wealth. On the other hand sould they decide to persue a college degree/career, you will have money set aside for that.

    Lastly, if you achieved your financial goals and have enough money after taxes to live comfortably then sell. 

    0Reply
  • James McGovern
    Flipper/Rehabber · Bloomfield CT · Member since 2020 · 1k+ posts · 409 votes
    1y

    Exiting real estate now is the best timing. Tenants aren't going to improve. Determining when to had enough takes courage 

    1Reply
  • Drew SygitBusiness Member
    Property Manager · Royal Oak, MI · Member since 2012 · 12k+ posts · 9k+ votes
    1y

    There are companies out there like Porch, Calvalry, etc. that you could outsource Maintenance to. 

    Or, hire your own handyman. 

    [email protected]248-209-6824
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    2Reply
  • Amit M.
    Rental Property Investor · San Francisco, CA · Member since 2013 · 1k+ posts · 1k+ votes
    1y

    @Stephen Jones  A few questions to ask yourself:

    1- is there lucrative property appreciation in your specific markets (due to building constraints, population growth, gentrification, etc.), that make it enticing to hang on to the properties for several more years?

    2- are rents expected to increase above average over the next few years, thus increasing income nicely. (somewhat related to question #1)

    3- what are the downside risks, such as overbuilding in your area, rental saturation, significantly higher operational expenses? (like insurance, for instance, or property taxes.)

    Your answers should guide your decision making. 

    If you decide to sell you can consider 1031 exchanges into more passive options such as, single tenant NNN properties or DSTs. They avoid cap gains taxes and solve the management issue, but have significant minuses IMO (namely high fees, and low/no appreciation). Another option is to pay capital gains and buy into syndications (you have a lot more options than with 1031 exchanges), although a lot of people have gotten burned recently with syndications when the market turned negative a few years ago.

    If you conclude that need to keep your properties but still want to lower management responsibilities, I’d look into hiring your own employees (a leasing/office person and a handyman at least.)  That way you can train them, and have direct control so they do the work at the level that you expect.

    Let us know what you decide to do!

    1Reply
  • John M.
    Investor · Fairfax, VA · Member since 2015 · 1k+ posts · 801 votes
    1y

    The answer is yes! Sell, Sell,Sell. You admit that managing is a pain in the butt even with the a management company. 10 Years is a good long hold time so i would imagine you have some equity. 1031 is an option into NNN properties, but be careful what you buy and the returns are low!!!... Trust me I know. Paying the capital gains is also an option. You can easily make 10-12% returns with limited risk on other peoples deals as a passive investor. If you want more than that then maybe you go chase that next deal on your own. Or do a hybrid approach. 1/2 of your profit into syndication deals and the other 1/2 into your own deal. I've been in your shoes and when you have cash and time on your hands the energy starts to flow again!!!

    0Reply
  • Austin McClainBusiness Member
    Real Estate Agent · OH · Member since 2021 · 348 posts · 602 votes
    1y

    If the management is the issue, consider looking into commercial. I've heard from investors in that space (especially triple net investors) that it has fewer headaches. The returns may change, but that could be a good option. 

    [email protected]614-710-4827
    0Reply
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