If its not someone you know the lender will dictate the terms.

Are you asking in terms of lending?

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.

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?

If transferring the property to an LLC, be mindful of the due-on-sale clause, and note that an LLC itself does not offer tax savings unless electing S-Corp status, which is rare for rentals.To maximize tax benefits, consider cost segregation, bonus depreciation, and short-term rental (STR) strategies, which could allow you to offset W-2 income if structured properly.

Cash flow is defined as the money left over after paying for all expenses, including setting aside a certain amount to cover projected expenses like maintenance, vacancies, or capital expenditures.EXAMPLE:Property Price: $250,000Down Payment (25%): $62,500Loan Amount: $187,500Interest Rate: 6.5%Loan Term: 30 yearsMonthly Mortgage Payment: $1,185Monthly ExpensesMortgage Payment: $1,185Property Taxes: $250Insurance: $100Maintenance (10% of rent): $250Vacancy and CapEx (20% of rent): $500Rental IncomeMonthly Rent: $2,500Total Expenses: $2,285Cash FlowNet Cash Flow: $215 per month 💰However, there are many other factors to consider.

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

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.

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

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