I looked at tampa but it's more of a suburban market. miami has over 21 zip codes you can go up to 8 stories in because of the affordable housing issues and it is the only city in Texas and florida in the top 10 most affordable housing needs ranked by city. it's not even close. 

Hey @Eian Trenkle, I'm actually dealing with the same issue on a STR of my own.

None of this is true in todays market though, you pay more per month to buy than rent anywhere in our area & frankly the country at this point, so it takes time for both having bought to be worth it and to move out and make cash flow, there are very few if any properties that are “value add anymore” I’d know because I look At 17 counties daily for deals & if there’s one I’d have bought one, heloc’s are bad debt ar this point, usually double digit debt, again all of these issues are solved with those but if your gonna live somewhere for a year or two he would probably rent and no amount of realtor ******** changes that, this market is different than a low interest rate environment and people owe thier clients at least to properly explain that to them.

Seems like your biggest issue is rent - what is market rent and what prevents you from achieving that rent?

If I were you I would lean towards properties with smaller landscaping issues if possible to minimize costs.

However, it did not go w/o issues and frustrations.

You are also physically there to address any issues that come up.

I have no experience there, but I am sure finding the right person to trust for a long time would be an issue here.

The builder has corrected grading issues twice before where there was standing water in my backyard, but it looks like the issue was never resolved.

My brother-in-law has been financially successful in real estate, but to avoid family issues, my wife and I have resolved to be self-sufficient.