We as a firm have investors working with us who have short term rental properties all over the US for example big and small.Finding a real estate-focused tax professional and one who can help with advisory and grow with you would be my suggestion to focus your efforts on finding.

If cash you can refinance, otherwise there is a seasoning period on the loan to get it.

They were not able to get the licenses in order to rent the others.If you already own the building, I would look at the longer term short term stay.

Side note, if you will be financing a condo that allows short term rentals, you will most likely need to obtain non-warrantable condo financing, not conventional.

I absorb information very fast and have gone through a good chunk of course work and books in just a short time.I am ready to start looking for deals.

I like your idea of short term rentals as I'd love to buy a place that I can use from time to time while having the mortgage covered with the rental income. 

I will try to keep this short and I appreciate any and all info given.

For the analysis of an arbitrage option, as well as other short-term rental opportunities, it entails a deeper review that not only involves understanding various market factors, but also the investor's estrategy and situation.

The section 121 exclusion doesn't apply, periods of non qualified use on rentals.

There is a community over there wanting to build up a boardwalk similar to New Jersey and return North Beach to it's prime (I think it had a boardwalk in 1915 before a hurricane).It has a lot of work to be done but it's in a good spot to downtown, right near the highway so easy to access and get to places all over the city whether you are going to the island for spring break or the university to visit college students it's a short drive.The area it self could be better but I think it has a lot of potential.