I literally want to vacation to San Diego.

I could sometimes get in 5-7 days once a year for a vacation but I'd pay the price when I got back. 

You can even plan vacations that are written off if using the sandwich method by doing work on Friday and Monday for real estate and the weekend is there so you do vacation stuff so all lodging and travel can be written off. 

Sellers may struggle to mentally shift from "owner" to "tenant," which can create challenges with boundaries and property care.Security Deposit:If you’re doing a temporary leaseback, be sure to collect a substantial security deposit to cover potential damages and ensure they vacate on time.

I would like to buy a future retirement home to get away from the cold winters but in the meantime would love to rent it out as a vacation rental.What are the good areas to consider and where would I get the most vacation renters and cash flow?

Over the phone (because I was on vacation), I called him and told him he needed to return everything or I would file grand larceny charges.  

The relatives are vacating. only 1 tenant wants to stay through ownership change.

I’m an investor in the Rochester market and also have experience managing from afar with some vacation rentals out of the area.

All are local to me in a non-vacation rental spot.

This is true regardless of how long you have owned a vacation rental.