I let VRBO and AirBNB handle that.Bottom line is you are taking a risk every time you allow folks to use the house.

It would be smart to do a full lease audit, estoppels issued, and tenant interviews.And if you are buying cash, there is nothing mandatory, since it is your money at risk. but again, physical condition inspections, understanding of tenants (they are a great source of information about issues with the property that the landlord may not know or may not disclose), surveys to understand accurate property lines, etc.

If there were no risk there would not be a reward of building wealth.

I once rented a 5bed/3bath in two days, just a week before Christmas when the ground was covered with snow and ice.Sitting vacant in the winter increases the risk of frozen pipes or other expensive problems.

Quote from @Steven Stanimirovic: Hi Rich,The prepayment penalties you’ve encountered are quite standard with DSCR loans, as lenders often structure these penalties (commonly called "step-down prepayment penalties") to offset the risk of early loan payoff.

It's important to understand that every investor comes from a different financial situation and as a different risk tolerance.

Like you mentioned, there is a risk for a mid term stay entering your top season.

but if you're that leveraged, it will be higher risk and very difficult to cash flow - so that is not something I would typically recommend.

Everything would be in your name and he would be at risk possibly even with a legal agreement.  

Thanks - will likely have to be an exception but definitely possible since the story "makes sense" from a lender's risk perspective