Are you asking in terms of lending?

Quote from @Joy Daniels: I manage short-term rentals in the Sarasota area, and I'm always looking for innovative ways to boost occupancy rates year-round.From your experience, what marketing strategies have had the biggest impact on keeping your properties booked?

Until the conditional use permit is applied for, an operator of a short-term rental is required to apply for a short-term rental permit.

Hello, I live in southeastern Wisconsin and currently have a long-term duplex in Wisconsin.

Google the term UBIT.Tom Wheelwright has a chapter on why you don't want to do this in his book Tax Free Wealth.

Secondly, I'd chat with a realtor and get some recs on lenders to truly see what you're working with in terms of buying power.

With that said, the income can still offset the cost of holding the property as a long-term investment.

I am here to create a business strategy that protects personal and business investments and mitigates risk,  procure a coach or mentor, and set up tax strategies to create long-term wealth for myself and my family. 

They also have a home vacancy tax in a lot of areas which applies to short term rentals. 

Prepayment penalties- usually 1-5 year terms.