- Current income- Hope of price appreciation- Vacation home to go to- Future retirement home- Store of value/hedge against inflation- Generational gift to the family- Alternative to traditional retirement investmentsI'll go first. 

If you go through a bank or traditional lender, they will report your mortgage, but at this point the DSCR rates are as good or better than the traditional mortgage rates, and the LTV are the same.   

There are traditional underwriting investment helocs but very conservative CLTV and DTI is taken into account.

Is it more because of a borrower not qualifying traditionally, property not qualifying, or they can get a better deal going private?

Are you aiming to refinance into a traditional mortgage?

Since your property is under an LLC, traditional credit unions might not offer the type of financing you’re looking for.

Too much risk.I like the idea of doing a land contract instead of a traditional sale but have never done one.What benefits would the land contract give us over just doing a regular sale?

STRs are traditionally seen as a lot more work than LTR because of the guest turnover but with tools that use AI to automate messages and send guests smart lock door codes at the right time...short-term can be almost as easy as long-term. 

Even back then there were a lot of high rise hotels where you could get a decent condo-style room with hot water, cable tv etc for really cheap ($15-20USD/night).

In a “subject to” transaction the parties have additional risk higher than a traditional sale.