Should I buy close or in growing markets?

Boston, Massachusetts
General Real Estate Investing
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Should I buy close or in growing markets?

Daniel Lenders
Member since 2025 · 9 posts · 5 votes

Hi everyone! 

I've been lurking here for a while now, but I am getting close to making the jump into real estate investing. I have a decent down payment in place, but I'm struggling to commit on a singular idea of what I want to do. 

My dad has been in real estate for 40 years now. He's a contractor and always bought close because he could go and fix things when they went wrong, update the property when the renters left, etc. 

I'm wondering about strategy. I'm currently in MA, in a suburb close to Boston. Should I stick close to be able to keep an eye on things? The market here is steep, landlord rights are harder than other states. 

I was also thinking about STR as well, but that is a whole other business.

I'd love a little advice for a new investor in RE to help give some direction! 

Thanks in advance! 

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Most Popular Reply

Melissa JusticeBusiness Member
Rental Property Investor · Phoenix, AZ · Member since 2024 · 519 posts · 1k+ votes
1y

@Daniel Lenders,

Hey there and welcome to the forum and props to you for taking that next step after doing your research. You’re in a great spot with a down payment ready and a solid mentor in your dad!

It’s totally normal to feel torn between strategies, especially when you're weighing what worked for someone else (like your dad) against what makes sense in today’s market. Given that you’re in Massachusetts, here are a few thoughts:

Staying Local:
Being nearby gives you peace of mind and control, especially with your dad's contractor experience, but MA is expensive, heavily regulated, and not very landlord-friendly. Your ROI may be lower and cash flow tight, especially as a first-time investor.

Out-of-State Investing:
You don’t have to invest close to home. Many investors today are building passive income streams through turnkey rentals in the Midwest and Southeast, where homes are more affordable, landlord laws are favorable, and cash flow is stronger from day one. Think of it as buying based on data, not distance.

STRs:
You’re absolutely right - short-term rentals are a whole different business. If you’re ready to manage guest turnover, dynamic pricing, and regulations, it can be profitable, but if your time is limited, you might consider mid- or long-term rentals for a more manageable start.

My Take:
Since you’re just getting started, I’d recommend keeping it simple:
Go with a long-term or turnkey rental in a cash-flowing market (think Birmingham, Indianapolis, Citrus Springs FL, etc.)
Use that first property to build confidence, systems, and passive income
Then explore more active or complex strategies like STR or BRRRR if/when you're ready

Happy to always help with identifying the right markets or running numbers.

You’re doing it right by taking the time to plan - excited for you to get that first deal under your belt!

Best of luck,

Melissa

[email protected]313-221-8718
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  • Jakob Mikhitarian
    Member since 2025 · 86 posts · 25 votes
    1y

    Hi@Daniel Lenders! I'd love to provide some value for you. I'm a investor focused agent out of NH and am familiar with some northern Massachusetts markets. It's amazing thst you are looking to get started into real estate investing. Do you think you could tell me what some of your goals are and what you'd like to get out of it are? Do you have a particular asset class/investing type you're leaning to--long term rental, STR, fix/flip, wholesale, BRRRR?

    1Reply
    • Daniel Lenders
      OP
      Member since 2025 · 9 posts · 5 votes
      1y

      @Jakob Mikhitarian I think I would like to BRRRR, but I'm not sure I have a whole lot of time/money for the renovations. I currently have a 9-5 and W2, so I'm trying to find other cash flows so that if my job gets gutted (AI is trying to take so many jobs), then there is a fallback on something secure.

      0Reply
    • Daniel Lenders
      OP
      Member since 2025 · 9 posts · 5 votes
      1y

      @Jakob Mikhitarian long term rental is likely the initial strategy I'd want to go for. 

      0Reply
  • Daniel McDonald
    Real Estate Agent · Beverly, MA · Member since 2019 · 358 posts · 308 votes
    1y

    I've been house hacking in Beverly, MA the past few years, that's the only way i could afford to stay close. I do recommend it if that's an option. 

    If not I STILL recommend buying close for that first investment. It's a peace of mind, easier, and dude it sounds like you have contractor connections which has honestly been the hardest part for me. 

    I also run a STR co hosting company and let me tell you it is a wayyy different vibe. You'll have to be ready to commit hard to make any real money off it.

    1Reply
  • Bernice RetzloffPro Member
    Memphis, TN · Member since 2024 · 234 posts · 100 votes
    1y

    Hello @Daniel Lenders!

    You're in a great spot with that down payment and a family background in real estate, which gives you a leg up. It totally makes sense to feel torn between sticking close for control vs. exploring more favorable markets. While investing locally has its pros, like being hands-on and leveraging your dad’s contractor skills, you're already seeing the downsides. High prices, tighter margins, and less landlord-friendly laws.

    If cash flow is your goal and you don’t want to feel stretched, you might want to look at out-of-state options like Memphis. It’s investor-friendly, has solid rental demand, and homes under $150K still cash flow well. Plus, property management teams are used to working with out-of-state investors, so you don’t need to be nearby to keep things running smoothly. If your dad’s open to advising from a distance, you could still use his expertise without being tied to a high-barrier market. STRs are a whole different beast, like you said, great upside but more active and regulation-heavy. If you're looking for a more passive, scalable path to start, a long-term rental in a proven cash-flow market might be the right first step. Just choose one direction and commit to learning as you go! Happy to help answer your questions & help you understand the Memphis market if ever you set your eyes on it!

    901-664-1949
    1Reply
  • Alecia LovelessPro Member
    Member since 2019 · 3k+ posts · 2k+ votes
    1y

    @Daniel Lenders I’d consider investing in southern New Hampshire. It tends to be more affordable than MA and is definitely more landlord friendly.

    Also if you’re close to Boston many of these markets are less than an hour away which is still pretty local to you.

    2Reply
  • Sasha Fukuda
    Walpole, NH · Member since 2018 · 66 posts · 34 votes
    1y

    I'd consider buying wherever your dad lives and paying him to keep an eye on it/ manage it.  

    0Reply
    • Daniel Lenders
      OP
      Member since 2025 · 9 posts · 5 votes
      1y

      @Sasha Fukuda unfortunately, my dad lives in Cali, almost as far as you can get away from me, in the LA market, where housing is currently out of control. He got in the market 2009 and has held for a while. It's not the same now as it was there. 

      0Reply
  • Drew SygitBusiness Member
    Property Manager · Royal Oak, MI · Member since 2012 · 13k+ posts · 9k+ votes
    1y

    How much have you learned from your dad?

    In our experience, a newbie landlord is always better off starting locally!
    As you referenced with your dad, you have more control.
    It's also a GREAT learning experience.

    Once you have a better understanding of landlording, you can expand OOS without getting taken advantage of.

    [email protected]248-209-6824
    Logical Property Management4.9469 Reviews
    WebsiteView Page
    2Reply
    • Daniel Lenders
      OP
      Member since 2025 · 9 posts · 5 votes
      1y

      @Drew Sygit I've learned some, but not a whole lot. What I've learned is that if you fix things fast and are helpful to your tenants(customers), then there typically is less hassle. 

      no matter what, there are going to be problems, repairs, upset people, and even lawsuits, when getting into landlording. You have to be willing to take on the risk of you want the reward. 

      0Reply
  • Melissa JusticeBusiness Member
    Rental Property Investor · Phoenix, AZ · Member since 2024 · 519 posts · 1k+ votes
    1y

    @Daniel Lenders,

    Hey there and welcome to the forum and props to you for taking that next step after doing your research. You’re in a great spot with a down payment ready and a solid mentor in your dad!

    It’s totally normal to feel torn between strategies, especially when you're weighing what worked for someone else (like your dad) against what makes sense in today’s market. Given that you’re in Massachusetts, here are a few thoughts:

    Staying Local:
    Being nearby gives you peace of mind and control, especially with your dad's contractor experience, but MA is expensive, heavily regulated, and not very landlord-friendly. Your ROI may be lower and cash flow tight, especially as a first-time investor.

    Out-of-State Investing:
    You don’t have to invest close to home. Many investors today are building passive income streams through turnkey rentals in the Midwest and Southeast, where homes are more affordable, landlord laws are favorable, and cash flow is stronger from day one. Think of it as buying based on data, not distance.

    STRs:
    You’re absolutely right - short-term rentals are a whole different business. If you’re ready to manage guest turnover, dynamic pricing, and regulations, it can be profitable, but if your time is limited, you might consider mid- or long-term rentals for a more manageable start.

    My Take:
    Since you’re just getting started, I’d recommend keeping it simple:
    Go with a long-term or turnkey rental in a cash-flowing market (think Birmingham, Indianapolis, Citrus Springs FL, etc.)
    Use that first property to build confidence, systems, and passive income
    Then explore more active or complex strategies like STR or BRRRR if/when you're ready

    Happy to always help with identifying the right markets or running numbers.

    You’re doing it right by taking the time to plan - excited for you to get that first deal under your belt!

    Best of luck,

    Melissa

    [email protected]313-221-8718
    4Reply
  • Sam B.
    Investor · Indianapolis, IN · Member since 2015 · 270 posts · 217 votes
    1y

    Yes stay local. Notice that most of the people on here who recommend investing out of state JUST SO HAPPEN to be selling rental properties in those very states. Weird huh?

    3Reply
  • Kate Sanchez
    Member since 2025 · 248 posts · 101 votes
    1y

    @Daniel Lenders  Buying close offers control, but growing markets can boost returns. Run the numbers, trust your gut - good luck on your first deal!

    0Reply
  • Kerlous TadresBusiness Member
    Realtor · Columbus, OH · Member since 2023 · 1k+ posts · 1k+ votes
    1y

    I would recommend starting by investing locally in MA, especially since you're familiar with the area and can keep an eye on your properties. Once you’ve gained some experience and feel more comfortable with managing rentals, you can start looking into other growing markets with better cash flow potential. This will allow you to expand your portfolio while keeping things manageable in the beginning.

    [email protected]614-490-1163
    Kerlous Tadres | Reafco Real Estate542 Reviews
    WebsiteView Page
    0Reply
  • Seth McGatheyBusiness Member
    Real Estate Agent · Milwaukee WI · Member since 2024 · 321 posts · 255 votes
    1y

    Personally, if people can afford it/their market allows it, being close to home is a great idea for first timers. There is a lot to learn on your first deal, no need to add the complications of a market you don't know, brand new contacts you need to meet and learn to trust, and limit options for quick person fixes to issues. I also think that a house hack is the best place for a beginner to start when possible. 

    All of that being said, doing something harder is better than doing nothing. If your market simply prices you out, then go for out of state investing. Most of you costal investors can just simply do better deals in the Midwest than you can in the costal markets. Especially when you don't have al it of capital built up yet. There is a reason BiggerPockets is doing a Midwest tour right now. 

    So if you decide your market just isn't feasible right now, reach out to agents across the Midwest and see if you can get one you like and if they can help you put a team together. If Milwaukee is one of the cities you consider, feel free to reach out and we can discuss if Milwaukee is a good fit for your wants and if you and I are a good fit to work together. 

    Best of luck with your decision and your investments! 

    [email protected]708-297-0996
    Seth McGathey - Shorewest Realtor4.914 Reviews
    WebsiteView Page
    1Reply
  • Joseph Bui
    Lender · Nationwide · Member since 2023 · 362 posts · 237 votes
    1y

    For me it all comes down to numbers. If you can make enough money each month locally, then buy local. If you need to go out of state, for those in high cost of living areas, then factor in fixes, property management, etc. If those numbers work better than local, buy out of state. Either way, as long as the numbers work, its better than doing nothing at all. Let me know if you have any questions around financing. Happy to help answer any questions or run numbers for you on any property.

    0Reply
    • Daniel Lenders
      OP
      Member since 2025 · 9 posts · 5 votes
      1y

      @Joseph Bui -- I definitely hear that. It often comes down to the numbers. I haven't started running any numbers and dont actually know what to look at for numbers. Could you direct me on a resource on what factors I should be calculating? 

      0Reply
    • Ken M.
      Investor · Get yourself trained before doing something inadvisable. · Member since 2024 · 3k+ posts · 1k+ votes
      1y
      Quote from @Daniel Lenders:

      @Joseph Bui -- I definitely hear that. It often comes down to the numbers. I haven't started running any numbers and dont actually know what to look at for numbers. Could you direct me on a resource on what factors I should be calculating? 


       Be careful, numbers don't always account for risk and hassle.

      2Reply
  • Charles ClarkBusiness Member
    Real Estate Broker · Milwaukee, WI · Member since 2020 · 306 posts · 209 votes
    1y

    @Daniel Lenders

    Hey there! It’s great that you’re taking the leap—and with a solid down payment and your dad’s experience, you’ve got a strong foundation.

    Staying local can offer peace of mind and easier oversight, but as you said, MA has tough landlord laws and high prices, which can squeeze cash flow. If you're open to long-distance investing, you might find better numbers and landlord-friendly markets elsewhere—with a solid property manager, it’s very doable.

    STRs are profitable but do require more hands-on systems, so be sure you're ready for that extra work.

    Pick one strategy to start—buy-and-hold in a stable market is a great first move. You’ll learn a lot just by getting in the game. You’ve got this!

    [email protected]414-719-6090
    Raise the Standard RE LLC55 Reviews
    View Page
    0Reply
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