If you can stomach some heavy losses in January and February (lowest revenue months in the Smokies) and May to a lesser extent, there may be better days ahead assuming this is your first STR.

😢In the end I might have to go ahead and replace the whole roof,  but I’m brainstorming now

You can't jump ahead to the building permit until the ZP is issued. 

Learn from other people's mistakes - It is SO EASY TO RUSH into real estate investing instead of finding people who have done what you want to do and work with them. 

Hey @Tyler Bilinovic, if you plan to purchase more properties go ahead and link up with an REI-savvy tax pro to form the relationship early so you're not scrambling as you're scaling.Even with just 2 rental properties an REI-savvy tax pro is worth the money.

If the market is slowing down, it might be better to hold and wait for a better time to sell.It's great that you're thinking ahead and considering all your options.

Rushing through this stage is a recipe for disaster.

That makes a difference, too.What are you rushing to get?

With the assumption that most of these will need to be addressed in a 5 year span, how does anyone come out ahead? 

I enjoy real estate the drive and the rush for me is closing deals finding them and helping others accomplish the same.