Time would be the biggest variable.Assuming the same repeatable services will have to be provided for STR & MTR, that are not provided for LTR, the costs may not be that different.Taking care of lawns, monitoring & paying utilities, taking calls, etc.Some services will be the same, but vary in frequency: cleanings, resupplying amenities, responding to inquiries, bookings, granting access, etc.

I had a calm today with Royal Legal solutions as I own three businesses in California and need to move them to a trust and start shielding myself and succession plan as well.

Like mentioned before, most investors are looking at creative financed options for deals right now in the area.Creative finance, putting a lot of cash down, or house hacking can all be viable solutions.

I am trying not to be discouraged and to embrace the mindset of looking at this from another angle, figuring out a more creative solution.

Regarding cash for keys, there are creative solutions.

Easiest solution might be just to extend the period of being able to collect that overage before it gets escheated to the state or taxing authority. 

Planning on enforcing fines and using a camera to monitor the area.

Based upon your statement, "Naturally, my heart goes out to this individual" is indicative that you may let emotions trump logic.Forward to your PMC and monitor their actions to start eviction ASAP if tenant is behind.You can also direct your PMC to offer to let tenant out of their lease early IF they cooperate with showings.If they fall behind, you can direct your PMC to offer Cash-for-keys to regain possession faster. 

I like Chris's solution if you do get a survey. 

Although I don't feel like I'm legally obligated, I'm trying to come up with a solution that works for both sides.