Rodrigues' recommendation may change this), but my next question would be, are there any cities/markets where 1 of the following are true: 1) You have family/friends that live there, 2) You travel there frequently (either for vacation, work, etc.), or 3) Somewhere else you've lived before AND know the area well?

All a mid-term rental is someone staying not permanently but longer than on vacation.

., known for its upscale appeal and strong demand for vacation homes.Properties in the Hamptons attract affluent buyers and renters, offering a high potential for appreciation and steady rental income.he property may have been undervalued due to its condition, presenting an opportunity to add value through targeted renovations.

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.

If you buy in a vacation area there really is no safety net other than desirability/location…I guess just don’t pay up too much.  

Start as a co-host and work under a vacation rental management company in the area to learn the ropes.

Hello everyone, I am analyzing the Indio, CA market as a short term rental investment and we'd love to speak to someone who is self managing their own vacation rental.  

For most vacation rental areas, irresponsible people are not renting homes.

So if the homeowner saves energy or goes on a long vacation, they still get charged 100%.

Vacation rentals are usually much nicer, are close proximity to attractions (beach, mountains, lake, theme park etc) and have nicer or more ammenities.