I've never been the landlord for a commercial property but have leased commercial property before - I leased through a commercial real estate agent who was acting as a leasing agent for the property owner, and the property owner was the one who collected my rent and is who I made repair requests to so personally haven't dealt with a Commercial PM before but will continue to follow this thread to learn more!

On another note, you have some fairly restrictive laws regarding private lending, consumer protection (seller financing to an owner occupant) and loan servicing in CA state so make sure you are allowed to do this on your own and understand the licensure requirements to lend, broker loans, and service them as well.

In the course of talking with them, the son mentioned separately to both me and my fiancé that he lived with his mom, had done so for a while, and was planning to take the smaller bedroom.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

I've done research in finding and analyzing properties so I feel somewhat comfortable in that regard.Here is a sample scenario below of a real property I've done some analysis on.

Yes, you should be able to do this, so long as the DTI for the Conventional loan works once the new minimum pmt on the Heloc is factored into your debts.

The LLC is the new owner of the property so a policy that is just in your name is not providing any coverage.  

So it sounds like they wanted to see you maintain deposit accounts with the bank and now they have possibly removed a discount they had given you when you took out the loans?  

In addition, I live with my parents so even househacking will still cost me over $400 a month, which is what I pay to stay with my parents. 

I find that enjoying so I continue to do it.