I was feeling unhappy with my initial coach so I wrote to the administrator of the course and asked for a new instructor.

What should I expect in terms of timelines, paperwork, or other administrative hurdles?

I have a good FT job in education administration, but I want to retire asap, focusing on RE (so, not really retiring, but you get the idea).

Section 8 is a process, it takes a few months to get everything up and running from an administrative standpoint.

I think a new administration brings new ideas and new people.

I would start asking questions about how the organizations you work with handle draws administratively and that should give you a good idea of how things will go. 

A good freind of mine set up an STR in a similarly lenient area and found that they could focus much more on guest experience rather than the administrative hassle.

The California government will deal with the damage the same way all governments do , they will find a way to raise taxes or get the Feds to pay for it ( that will be difficult with the new administration ) Here is what I find ironic , California has C.A.R.B. to pass regulations on vehicle emissions .

Rent control measures, burdensome employment regulations, and excessive administrative requirements exemplify this.

You could seek administrative roles, leasing assistant positions, or internships to learn the business paycheck.