I would probably personally go for a less 'complicated' deal (with the loan and family factor stuff), but having the luxury of taking over what you are saying is a sound VR business has it's benefits as well. 

Everyone expects luxury in a vacation.

I'm in my mid-20s, I live in NYC and currently work as a property manager for a medical institution that is continuously expanding their real estate portfolio consisting of luxury high rise apartments.

However, I'm dealing with A-class luxury properties, so they may or may not be a fit for your property type.I hope that helps!

I believe I read less than 1/3 of luxury car owners are millionaires.  

Also while this isnt generally the market people on here are buying in, luxury listings...sometimes you can sell these for more off market than on. 

Should the tenant claim the landlord changed the locks and removed her property, the landlord could be responsible for all sorts of damages such as lodging fees, replacement of lost / destroyed property, punitive damages, and attorney fees.

For what sounds like a non-luxury, basically commercial property, that's REAL slim pickings.

Depending on your neighborhood, things like cap rate can be incredibly high (war zone), or fairly low (luxury properties).

In Santa Monica I found that it attracted businesses with tech or engineer teams working on month long projects and looking for lodging and business men traveling with families.