You need some descent reserves to be a larger landlord, because you don't get a choice when the AC unit goes out, or the hot water heater floods the upstairs unit that then floods the downstairs unit.  

Sometimes stuff still goes wrong, but that's on me since i made the choices and decisions.

Totally get what you mean about using fear to make smarter choices and stay focused.

Given the parameters of needing to be remote and trying to maximize monthly passive income while acquiring more/larger properties either through more SFH or 5+ multifams, if you were in my position, what would y'all do?

If one of the units you will occupy is larger in GLA/bed/bath count its okay or if its closer to work or school.

In retrospect...this was probably a "meh" financing choice in my opinion, not sure if I would do it again.  30 year terms, no fear of balloon, that's great. 

You can adjust prices on booking.com so that they are higher to make up for the larger commission fees. 

There are choices for the comparable sales inputs, discretion used for the adjustments, etc. 

I have a feeling that his choice will be the latter....hence my prediction..."

We are here to learn and get as much info as possible to make great choices.