My guess is though that as you and I suspect it is the "flovor of the day" as you say and a pretty bad flavor at that. 

So, make sure you are always looking to acquire properties, but I wouldn't hold that goal over your head because you might make bad decision to get your number when the deals just aren't there.

We don’t know any PMCs to recommend in the area mentioned, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

Changing or presenting the reservation, payment schedule, or pricing in bad faith to avoid mandatory Vrbo compensation.

Things have to go really bad from here, as I see it, for the office to underperform alternatives in the next few years, from a cash flow perspective. 

If you don't have a good foundation(bad debt paid off, $$ saved up) I would first focus on that.

Cause if he learns bad habits now, like living above his means or not saving, they'll be hard to break.

2) "asking me not to post anything negative (which I’m clearly not doing)" - How is this entire post NOT making them look bad? 

.#2 can be a bad option in the middle of winter when renters are harder to find.

If you could stomach the negative cashflow or get creative holding is not bad.