These people seem to stay for years which makes it easy for me to self manage.

It seems, obviously, that the method is strongly focused on the refinancing of the property post rehab.  

Her Facebook page seems to bear this out.

Yes, strange, but this is what the Regs seem to say. 

We like the software, but the consulting service seems taking a bit too long... we would like to have someone to help us out with set ups, automation and a general marketing plan...

I think this may be a built in functionality of the Turno app, but I don't use Turno and my cleaners don't seem to offer that as part of their standard process.

Otherwise with the dwindling tech sector in SF, and the remote work (2-3 days a week) that is most likely here to stay, it just doesn't seem like a strong mid term market to me.

It seems like every city, county, and state has its own rules, permits, and tax requirements for short-term rentals, and I’m finding it overwhelming to navigate all the different layers of compliance.For example, some places require business licenses, transient occupancy tax permits, or even special zoning approvals.

You said: "This seems like an odd strategy - purposefully invest in an asset that loses value, with the hope that it will regain value to save a little on taxes... 

I do agree with the others that the officer doesn’t seem to be doing their best here and further due diligence/follow up on your part might be useful.