My end goal is to be wealthy enough to have nice things and for my wife and I to not have to work a regular job anymore. 

in the process so I won't be able to regularly visit an office.

The most important factor on the income side of your STR is the # of occupants your property can sleep.

A good operator should be communicating regularly with the investors and sharing the good, bad, and most importantly the ugly.

I converted my property from a three-family to a four and am now having to get a commercial insurance policy instead of regular homeowners -- it's not a big deal, but it is annoying.

Has the current owner been completing regular inspections? 

Coming to meetings he didn’t need to and didn’t even know he was going too, meeting with us regularly at the rental property to go over construction needs, staying extremely on budget and the willingness to work with us on three separate projects is great.

I don't know anything about selling with them to answer your question, but regardless of what they offer, I'd also check in with a regular real estate agent as well.

If not, then I'm not sure why you can't get a regular conventional investment loan. 

BLUF: Mother-in-law has spent many years vacationing in Mexico regularly, wants to buy a beach front condo in Puerto Penasco as a VRBO.