I’m just uncertain of where to go from here. have others dealt with similar issues?

I've seen some cheap California properties, $299,000 to low $300,000s a few in SoCal and one in the Bay Area (highly unusual for that low).

The only "unusual" thing about this part of the transaction as compared to a traditional home sale is that the owner I'm purchasing the home from will hold the mortgage for 2.5 years.

I have an unusual situation:I own a property which is under contract to sell to my tenants on Nov 1.

In fact, it might be useful to keep your job until you reach a very solid position.People are in a hurry to get out of their jobs, but things happen, and a steady job with benefits has a lot of value in uncertain times.Now if you flip hamburgers, I totally understand.

I'd expect that with some more due diligence you could get much more specific than with that range.2) Per my understanding, it would be very unusual for the tenant to pay the HOA fees.  

It would be prudent to have an additional exit strategy if and when the city becomes sincere in their regulation efforts, or, more likely extorts enough money from AirBnB'ers that it is no longer unusually profitable.

I've never needed a resume (thank god) so I can't really critique that part but I will let you know that  "Immaculate" is spelled with an "i". it's a bit of an unusual use of that adjective,  but I think it works.

It's been an issue in Silicon Valley since the late-00s: landlords holding out on startups as the rental market heated over; startups frustrated with the multi-year lease while trying to get even the most basic product off-the-ground and uncertain if they'd even be around in a year.

Keeping a property that you are uncertain about is always risky because you know the value today but what about tomorrow.