I spent weeks trying to get a handy man to fix a sliding door.

HOWEVER, there are certain areas that are dealing with different layers, like.. massive migration to the Southeast Region of the US, which means tourist areas near those areas (beaches and mountains) are still exploding and breaking records for STR market cap (money spent by guests on rentals).

You can use the cost of the land and the other costs you have already spent toward the down payment, so I suspect you won't have to inject anything else into the deal.

What if the new owner backs out of the job and gives it to their "regular guy", will the original contractor come after me for any expenses/materials spent?

The money spent on the flip will be a write off from your profit and shouldn't be taxed regardless. 

I spent 40k in the first year bringing it to habitable and then I jumped though all the ******* crazy hoops the town made me jump through to get one of the only 6 STR permits they issued that year.

This means more time and money spent on marketing and preparing the property for new tenants.Wear and Tear: Student tenants may not take as good care of the property, leading to more frequent repairs and maintenance.

Also, any stone fabrication you know in the area to spent minimum?

If they spent money on credit, title, etc., its all a part of doing business.

Scroll down the page and look for cities above the line for good performance.https://www.airdna.co/blog/best-places-to-buy-a-va...A word of warning - from someone who’s spent waaayyyy too long playing around on the AirDNA web site: they measure profit as revenue minus mortgage.In many cities, a large chunk of the high airbnb revenues come from very specific highly desirable properties in highly desirable areas (e.g., baller properties that are downtown or oceanfront or lakefront, etc).