Please HELP a Relative Newbie Strategize!

Greensboro, North Carolina
Real Estate Deal Analysis & Advice
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Please HELP a Relative Newbie Strategize!

Brian Siedenburg
New to Real Estate · Greensboro, NC · Member since 2024 · 12 posts · 22 votes

Hi! Context first since I know a lot of posts end up being f/u questions to the original with these types of things. 

Goal: 

Cashflow first, appreciation next. 

Current REI status:

2 properties in Greensboro, NC, one LTR (the one Im asking advice on today), and my primary residence which Im currently house hacking and airbnbing the rooms quite successfully (covers mortgage at minimum). 

Financial status: 

About 25k in the bank and other money in various markets (but not a ton, maybe an additional 20k). Dont make a lot, W2 is about 58k/yr. Airbnbing the rooms + small cashflow on the LTR should bring in about 20k this year at least. I just live extremely frugally. 

Dilemma:

Basically, Im trying to decide whether to keep my LTR or 1031 exchange it into something else.

I "cashflow" about 290/month on it that basically gets put aside for maintenance. About 50k equity in it right now. It's built in 1955, roof is 20 years old (I might be able to get an insurance claim on that but not sure...Long story), HVAC is 22 years old (and I will likely have to replace it in the next month), hot water heater is just as old, electrical is only grounded in half the house (it had an addition), but my biggest worry is 70 year old galvanized steel pipes in a slab foundation. Its not in a BAD location of town, but its also not in the, lets just say, top 5 desirable locations in town either. 

Not making a lot with my current job, Im really worried about the big capex that might be looming. 

I would exchange into either:

- A smaller airbnb in the NC mountains (the idea of also using this myself is very appealing) or potentially beach (but insurance is a turn off here) 
- A value-add around here where I can get it cheap but put in less than the ARV
- A standard LTR around thats been updated and doesnt have major capex looming. 

What would you guys do? What other aspects or questions or solutions should I be thinking about? Thanks so much in advance!

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Melissa JusticeBusiness Member
Rental Property Investor · Phoenix, AZ · Member since 2024 · 518 posts · 1k+ votes
1y

@Brian Siedenburg,

Great breakdown and kudos for being thoughtful about every angle. You’re making smart moves on a lean income and have built a solid base.

Here’s the short answer:
If capex risk is keeping you up at night, and you're sitting on ~$50K equity in a tired asset that’s barely cash-flowing it may be time to 1031 into something stronger that aligns with your “cash flow first” goal.

You’ve got 3 good options. Here’s how I’d think through each:
1. 1031 into a Turnkey LTR (Midwest or Southeast)
Why: Maximize cash flow, zero rehab risk, newer mechanicals.
You could buy 2 updated SFRs or a duplex in places like Akron or Canton, OH, Memphis, TN, or Columbus, GA, for under $200K each.
With property management, this stays passive and avoids the big-ticket capex surprises.
Likely $200–400/mo cash flow per property = $400–$800+/mo total.

Perfect fit if you're trying to grow slow and steady while minimizing surprises.

2. STR in the NC mountains
Sounds fun, but make sure:
It’s a STR-legal zone.
You can self-manage or have a reliable cleaner/PM.
Seasonality doesn’t eat into your expected numbers.
Personal use is a big bonus, but don’t let that cloud the math.
Good move if you want some lifestyle return + are confident in your STR analysis skills.

3. Value-add local deal
Riskier with your current capital reserves.
You'll need to fund repairs upfront so unless you find something cheap with light cosmetic updates, this could eat up reserves fast.
But you’re local, so managing a light rehab is within reach if the deal is strong.

TL;DR Recommendation:
With your goals and budget, I’d lean toward 1031 into 1–2 updated cash-flowing rentals in stronger markets. You’ll reduce stress, grow income, and build equity with less risk.

Always happy to share turnkey deals with capex already handled, tenant-ready and PM lined up so you can keep scaling without the maintenance headaches you’re currently facing.

You’re doing awesome! Keep moving forward smart and steady.

Best of luck!

[email protected]313-221-8718
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  • Melissa JusticeBusiness Member
    Rental Property Investor · Phoenix, AZ · Member since 2024 · 518 posts · 1k+ votes
    1y

    @Brian Siedenburg,

    Great breakdown and kudos for being thoughtful about every angle. You’re making smart moves on a lean income and have built a solid base.

    Here’s the short answer:
    If capex risk is keeping you up at night, and you're sitting on ~$50K equity in a tired asset that’s barely cash-flowing it may be time to 1031 into something stronger that aligns with your “cash flow first” goal.

    You’ve got 3 good options. Here’s how I’d think through each:
    1. 1031 into a Turnkey LTR (Midwest or Southeast)
    Why: Maximize cash flow, zero rehab risk, newer mechanicals.
    You could buy 2 updated SFRs or a duplex in places like Akron or Canton, OH, Memphis, TN, or Columbus, GA, for under $200K each.
    With property management, this stays passive and avoids the big-ticket capex surprises.
    Likely $200–400/mo cash flow per property = $400–$800+/mo total.

    Perfect fit if you're trying to grow slow and steady while minimizing surprises.

    2. STR in the NC mountains
    Sounds fun, but make sure:
    It’s a STR-legal zone.
    You can self-manage or have a reliable cleaner/PM.
    Seasonality doesn’t eat into your expected numbers.
    Personal use is a big bonus, but don’t let that cloud the math.
    Good move if you want some lifestyle return + are confident in your STR analysis skills.

    3. Value-add local deal
    Riskier with your current capital reserves.
    You'll need to fund repairs upfront so unless you find something cheap with light cosmetic updates, this could eat up reserves fast.
    But you’re local, so managing a light rehab is within reach if the deal is strong.

    TL;DR Recommendation:
    With your goals and budget, I’d lean toward 1031 into 1–2 updated cash-flowing rentals in stronger markets. You’ll reduce stress, grow income, and build equity with less risk.

    Always happy to share turnkey deals with capex already handled, tenant-ready and PM lined up so you can keep scaling without the maintenance headaches you’re currently facing.

    You’re doing awesome! Keep moving forward smart and steady.

    Best of luck!

    [email protected]313-221-8718
    2Reply
  • Brian Siedenburg
    OP
    New to Real Estate · Greensboro, NC · Member since 2024 · 12 posts · 22 votes
    1y

    Very thankful for your reply! 

    Great advice. Although I just found out that you have to have the house as a rental for at least 24 months before 1031-ing it (is that correct?). One detail I left out is that I only turned it into a rental in March of this year after I moved out and bought this second place. 

    Although I still am leaning towards just selling it outright. I did live in it for about 15ish months so I understand I may get a prorated tax reduction amount based on the 2 out of 5 years rule. And I bought at a high point in the market in Oct 2023 so Im not sure how much profit Ill make - But it still sounds like rolling it into something safer is smarter for my context. 

    Thanks again and I very well may be reaching out. 

    0Reply
  • Pat LulewiczBusiness Member
    Realtor · Raleigh NC and Greensboro, NC · Member since 2019 · 391 posts · 392 votes
    1y

    Generally have to keep a property for at least a year to 1031 it. Remember you'll still have realtor commissions so that takes a piece of it out.

    Have you done enough homework on a 1031 to be prepared for it? You have to move fast within the time requirements. Plus what interest rate is the house you want to sell? Will you be able to buy something to replicate that cash flow with current rates? Are you going to be able to qualify for a loan on a new one with current rates given your W2 job and cash flow.

    Both mountain and beach are great options and both perform well (insurance isnt that bad when you cash flow a lot of STRs), however have their own complications, particularly if you're going to manage remotely from the triad.

    Personally, it sounds like you're doing well in your investing career and making good money. You're setting aside funds for capex and have savings. Budget for and ake the $10k-$15k hit on looping capex when it comes and then that property will be capex-free for 15-30 years.

    0Reply
  • Dave FosterBusiness Member
    Qualified Intermediary for 1031 Exchanges · St. Petersburg, FL · Member since 2013 · 9k+ posts · 9k+ votes
    1y

    @Brian Siedenburg, Funny enough, there is no statutory holding period before you can do a 1031 exchange, but usually at least 12 months is recommended hold, and longer is always better. However, there can always be specific circumstances that might cause an investor to prematurely sell.  So it really comes down to how you demonstrate your intent to hold onto the property for productive use.

    The 1031 exchange can be a great tool to scale and access more cash flow and appreciation since it allows you to use all of the tax to reinvest into larger investment properties. What you decide to reinvest in will be determined by what aligns with your financial goals and what kind of potential the local market allows.

    The 1031 Investor5137 Reviews
    WebsiteView Page
    0Reply
  • Drew SygitBusiness Member
    Property Manager · Royal Oak, MI · Member since 2012 · 12k+ posts · 9k+ votes
    1y

    Why not move back into your original house;

    1) Start fixing it up yourself

    2) STR or MTR your bedroom in the other house

    [email protected]248-209-6824
    Logical Property Management4.9451 Reviews
    WebsiteView Page
    0Reply
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