u/Munkreadsreddit

I’ve been an out-of-state investor in Cleveland for four years. I started by buying four properties in year one, before I really knew wtf I was doing (one cash; 3 debt), but I’ve decided to shift my strategy - I want to downsize to just two properties, both fully paid off. I know the conventional wisdom is to leverage debt to grow, bla bla bla but I have a decent full-time job and I’m prioritizing peace of mind, less debt, and fewer headaches. Especially as I have learned a lot & want to use new cash to invest in better properties.

Anyway, I just closed my first sale today to start this transition. Now I need to decide which of my remaining two to sell so I can pay off the other one. Both would likely sell for about $130k. Here is the breakdown:

Property 1 (Duplex): Older building, but I’ve put in a lot of work (new plumbing, full bathroom renovations, resealed basement, etc.). I can get about $1,800/month with non-Section 8 tenants (which I prefer). It’ll still have some maintenance issues being an older building, but it feels stable - appliances & major systems are in good shape.

Property 2 (Single-Family, 1,800 sq. ft.): I Built from the ground up in 2023, so it’s brand new. The catch is it’s in a really bad neighborhood (my first rehab so I went cheap property to learn but it was down to the studs & rebuilt well), meaning I’ll be 100% dependent on Section 8 & it’s huge. 1800+ SQ ft. The tenants are kinda messy (but stable), so turnover cost I assume will be high every time one moves out, appreciation low & heavy reliance on the single tenant. I’m thinking well high, before issues start.

My Dilemma:
I’m leaning toward selling the brand-new house. My gut says that even though it’s newer, the location and the Section 8 requirement will lead to more turnover headaches and risk in the long run. I think the duplex, despite being older, will be more manageable once I finish the final bits of work.

Does this make sense, or am I overlooking something?

Would love to hear your thoughts.