Please HELP a Relative Newbie Strategize!

[Brian Siedenburg]

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!

[Melissa Justice]

@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!