Obviously need to check zoning and set up costs etc. 

You have to complete Schedule E if you have rentals.You should check if the turbo tax premier version allows the filing of Schedule E.With that said, using a software like Turbo Tax will assume you to understand what is deductible.If you work with a tax professional, you are more likely to have an accurate return.

But last I check their requirements for LTV/DSCR was very strict.   

Theres someone living in the side that I will be occupying until the 1st of February, but since I JUST became the owner, would it make sense to reach out and ask them something like "Hey its __ the new owner, just checking in to see how you're doing.

@Jacqueline Wright  Every auction is different so the first items to check: do they allow financing if you win the auction? 

I know most investors would say it's crazy to invest in older condos for rentals but in Raleigh it seems to be an overlooked opportunity.

Here are a few suggestions on how you can maximize the wealth of information available: Check out the blogs and podcasts, or take advantage of the search feature (magnifying glass).

Depends on the town’s rules, though, so check that first.Renovation Loophole: Some places let you raise rents or get out of rent control if you do big renovations.

Since you're in Destin, you might want to check with local firms that have experience with STR-heavy communities, as they’ll be familiar with the risks and requirements.

Here's a link https://www.mass.gov/how-to/check-a-home-improvement-contrac...IMO vetting contractors is important.