(permitting, taxes, etc)

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.

Not sure your strategy here but just throwing some ideas your way.Check building permits to see what's happening in town.

Address key issues in the report, again prior to listing.Offer a home warrantyShow copies of permits and permit inspectionsKeep in mind some of what you can demand in the contract will have to do with the market.

Thank you @Joyce Beck... unfortunately with this forum we cant post any websites or any specifics for our projects.. so we wont be able to get any real help of advice for our specific needs... as I was hopingIts been a challenging climb I tell you on this level of Project... and Yes I keep forging ahead with Gods leading, guidance and strength.. step by step.Most are fascinated at how far I have come and now need to find additional investors to get to the next level... constructionI have permits and everything nowI even have a SBA approval but we are over the $5M limit so need Bridge financing to close the GAP of $2.7MI have come too far to stop now... 

However in my city a permit is required to list on Airbnb for 30 consecutive days or less.

I've paid for the land, architect/permit fees, excavation and foundation out of pocket.  

Here in Austin that does require a permit, but those can be obtained with the right planning. 

Before I put a offer in I looked to see if there were any open permits, there were none.

You will spend 2x as much as you think and it will take 2x as long as you think and you will get 2x fewer permits than you should because you will use 5x the number of contractors you should.You are thinking money first which is why it won't work.