I am looking for the same thing and wanted to check in with the BP forums so figured i would revive this old thread.

Obviously need to check zoning and set up costs etc. 

Given the property is located in the Poconos and the property is vacant more regularly as an STR there are proactive measures  you should  be taking such as making sure there are heating sources so that the plumbing does not freeze and ensuring there are no blocks in the plumbing lines with routine checks.

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.

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.   

Quote from @Jeremy Torres: Quote from @Patrick Drury: @Jeremy TorresIn terms of what's a good offer you would need to check with an agent or do some research on your own of looking at comps in the market.

Make sure the lender you choose has a strong background in this type of lending...check them out on Linked In to see their experience level.

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

Bigger Pockets is a great place for education and networking and is full of great content.I recommend that you check out the following resources:1.