Finding a REAL DEAL is #1 biggest issue.

You may not make as big of a return, but the downside is a lot less.

The downsides are you’re paying taxes that will go away at their passing.

Sounds like that might be your biggest problem.

Potential upsides and downsides?

If so, one downside is turnover - you would likely have different tenants every year.  

The biggest problem with people doing driving for dollars is that they do not understand the concept of motivation.People often look for distressed properties.

However, one of the downsides is that if you're going to use a property manager, you have to use the on-site Property Management company in order for your guests to get access to the community amenities.

The biggest vacation rental house at the time was a massive 7 bedrooms.

@Maximillian Engram There are no downsides if you plan to actually focus on sales and invest.