It's definitely a lower income area, and will not attract renter's for Mid-term or short-term rentals.

Are you a new homeowner or investor navigating the maze of real estate taxes?

Also, my tax bill was super high this year since my property didn't really require any maintenance last year, and this would be a beneficial write-off as it would buy back time and ensure a quality property.

,When you 1031, you carry your adjusted tax basis from the old into the new. 

Of course it’s not as simple as it appears.....lots of hidden costs, taxes, insurance, preservation, etc. and much depends on the jurisdiction as to length of foreclosure process. 

The value of the condo went up (that's good), but the rental situation in Sarasota went down.Long story short, I can hardly make the mortgage with the forecasted rental income for a midterm.

STR with a 50% occupancy monthly income I'm guesstimating to be about $2,037. 

Unless paired with the above, these are usually thrown out in tax court. 

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with zero or negative relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560, little to no good tradelines, lots of collections & chargeoffs, recent evictions.

And then they deducted $10k/mo is lost rent from their taxes.