You already said he wouldn't qualify to rent the place if the insurance company wasn't paying, so then you'd have someone staying there that couldn't pay and you'd be forced to do a long drawn out eviction (assuming evictions have resumed by then and no additional moratoriums had been put in effect). 

Its a subject-to purchase, effectively with no agreements. 

PM is a skill like anything else and it will take him time to get up to speed to be effective at this.2.

I would look into BRRRR method options to leverage your cash more effectively and get to your goals a bit faster.

If Covid does not go away and this next stimulus is not as effective as we need it to be, what is some insight on a POTENTIAL larger scale eviction?

In fact, I feel that part of the broker's responsibility is Shiny Object Slayer:  help their agents discern their vision, plot a path to that, and stay the course. 

I've read that Absentee Owners get multiple offers every week in some markets.Two new lists that are proving effective are Homeowners with Low Financial Stability Scores (FSS) and Seniors with Long-Time Ownership.Good luck

Also, prices were somewhat artificially inflated and lenders have become more conservative, effectively moving prices back down to a more authentic level. 

One play you could do is a cash out refi if it doesn't effect your debt service too much, and still cash in on additional appreciation in the CA market.

As stated above, as long as you get an experienced 203k lender on your team, and effectively compile a list of 5-7 licensed, insured, and bonded contractors to bid the project, it’s absolutely worth the endeavor.