Quote from @Alyssa Dinson: Hi everyone, I live in California and have been meeting a lot of investors who prefer to invest out of state due to California being so expensive as well as the aggressive tenant protection laws we have here.

Just my personal opinion - get a mentor or a person who already has good experience running STR business, preferably in your area (but not 100% required). 

I'd prefer a small business.

Though he prefers to reposition existing multifamily properties, he has also subdivided land, built homes, and constructed self-storage.

I’ve been a serial house hacker in the greater Boston area so happy to connect and share some lessons learned.Multifams inventories are quite low depending on your budget and location preferences.  

Knowing my situation, if my wife and I were doing something like this, I'd be OK with buying something sooner and cheaper, but my wife would prefer to wait a little longer to save more to buy something nicer.

Your son is likely paying more than the property is worth, by definition, as the seller would almost certainly prefer a similar offer that was not subject to. 

I am with Nabers and would prefer to move to a platform that provides robust book keeping and filing services. 

They are too much of a gimmick and most tenants prefer to have the bottom-line expenses.

Given the photo of that fix/flip, I assume you're OK with a "fixer upper" or would you prefer a turn-key rental?