I live in Tampa and I have to admit it does drop a touch below 55 sometimes. I think this last winter it got around 45. I came from Kentucky so any temperature above freezing is great in my book. The cold spell lasted about 4 weeks I think.
Anyway getting back to the condo vs. house. The condo is for sure the easy way with maintenance, and streamline a renting roster. As you know the Tampa Bay area has some very nice beaches. They are a hot tourist area. For the $250K price point you can find a nice condo but you also said you wanted to minimize HOA/ condo fees. Often those can be high and can destroy profits if not careful.
I am curious what do you consider high HOA/condo fees? I know you mentioned a home to by and rent but then once you work in remote cleaning crew, property management, repair expence, along with ALL utilities. Running a SFH (single family home) as a weekly rental becomes more difficult. You could pay a company to do all those things but once all the cost and expenses are paid. I would guess it would be close to your HOA/ condo fees.
Just something to think about. Once again I am curious about what your thoughts of HOA cost is to high? Trust me I feel the same way about paying a HOA for full ownership of a investment.