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seeking financial / life advice - condo, house, apartment?

discussion

I'm a 28 y/o M. No wife, gf, or kids. I have my own business and travel for work as a drone pilot, mostly for T-Mobile, Verizon, and AT&T, going cell tower to cell tower all across the eastern half of the U.S. I often sleep in my car (Tesla Model X) while on the road. I travel about 150-250 days a year. I currently live with my parents whenever I'm home in Cincinnati. I've driven as far as Florida, Maine, and northern Michigan for some sets of sites. I spend a lot of time on my own, so it's nice to come back to Cincinnati, where there are family and friends. I have about 20k in individual savings and 35k in retirement. 20k left on 5-year car loan. gross income of 103k in 2025 but 40k worth of deductible expenses (miles, hotels, 50% meals, camera tech, equipment, health insurance, etc.).

I'm trying to figure out where / how I should live in a year or two once I can save up enough. My setup now is fine: no rent at home, and sleeping in a car/hotels while traveling. But I'd like the independence of having my own place.

I'm gone so much of the year that I know I'd feel guilty renting an apartment and wasting money if I'm not there for 2-3 weeks at a time.

Buying a house, I think I'd feel stressed not being able to keep an eye on the property and spending all my time at home catching up on typical house-ownership chores like keeping the lawn tidy, fixing things, etc.

I think I'd be happier owning a condo and not having to take care of any exteriors and having a community to come back to. A gym, pool, communal hangout spaces, etc. would be nice to come back to after a long road trip. Thinking I could also Airbnb it out when I'm away on trips. With HOA fees, wondering if I'd feel guilty paying that if I'm not always home, similar to how I'd feel renting. While there's more flexibility with renting a place, ownership would be nice to build equity and possibly sell it after 7 years of this job, once I'm ready to settle down with a job that requires less traveling. Even if I only make a few thousand dollars after selling it, I'd feel better knowing I got to live somewhere for 'free' (assuming my profit would equal total HOA, loan interest, and tax fees).

In a perfect world, I'd have my friends as roommates and rent, but none of my close friends are looking for that right now. Living with semi-close friends or strangers, though, would feel awkward because I wouldn't be around enough to develop a close relationship.

Thoughts on buying a condo? vs renting, house, apartment, living w/ parents?

Posted Apr 6, 2026, 1:13 AM UTC

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