I have a guy who has been here since July, but I renew his short term stay for two weeks at a time, every two weeks.

When running your numbers, if purchasing a home that isn't new construction and less than $1MM, I would estimate 1% - 1.2% of the purchase price as your annual insurance premium. 

In a great and popular location with rising rents and upside on price with renovations but also that will cost in the short term to improve the property. 

Investment also spiked in Class A Short-Term Rentals (STR) and investors started paying higher and higher prices based upon anticipated STR rental rates, that exceeded sustainability based upon Long-Term Rental rates (LTR).

Return:Finishing the basement and adding bedrooms can add significant value, especially if your local market places a premium on additional living space.

I am also a member/subscriber of Vodessey, Short Sale Prophets Basic, and several others. 

I've never seen a new STR law that didn't grandfather in existing permitted short-term rentals.

I'll work with an attorney to assist with drafting that.Q2: Yes, I'll talk to my CPA but we'll most likely hold the property for at least 1 year under the LLC given our timeline to design, permit, build and sell the property, meaning I should avoid short-term capital gains.  

@Olecia Williams I am local here in Florida and help clients all the time purchase second homes that they short term rent with 10% down with zero issues.

.- Short-Term Rentals in Non-Traditional Markets: Secondary markets like Florence, Alabama, are ideal for short-term rentals.