Happy to connect if you have specific questions or need assistance with setup/ongoing management.

Is that a SF area specific rule or is one of my lenders mistaken?

Without knowing your level of experience, it's hard to provide specific feedback but one thing I am assuming is you would like to create a long term relationship with this individual so you want to make sure you treat their money better than you'd treat your own.   

I am not looking for $ amounts, but rather specific concerns to be focused on.  

What specific date did the tenant move out and when was the MoveOut done by the PMC?

They are specifically built to be STR and you won't have to worry about the HOA or city changing the rules on you. 

I have a lease that I created using Avail that is similar to my leases on my other medium term rentals but I have a few clauses on occupancy that are specific to my house hack.

I've been trying the websites for the Census Bureau, Urban Institute, and Pew Research Center, but still can't find the specific data I'm looking for, leaving me with four questions for you:1.

(I did a 15 year as i want it paid off if I decide to live there as I don’t deduct personal interest.) it also generates almost $20k in depreciation helping to offset my other income and traveling to it on business allows me to stop and see my family that live near by. 

Get several bids, be extremely specific with your scope of work, and then if you need a lower price, modify the products you have chosen.