But it is very risky and you can lose all of your properties if things go wrong.

When you have a duplex and tenants on both sides stay for ten years, it almost guarantees that something isn't right.I would study your market and determine the value of your rental, because I bet you are losing money every month.

Why would I be cash flow negative and losing money for years and years?"

The owner seems to want to not lose ownership of the account altogether.

Average rents are $1,250 (Again Zillow) Easily a losing propostion.

Mailing/emailing a notice to "start the clock" doesn't cost much and should be done to NOT lose time if tenant doesn't pay.

.* Automate Follow-Ups to Stay Top-of-MindMost wholesalers lose deals because they don’t follow up consistently.

1) Yiu REALLY need to know what CA will  allow you to do, I don’t know, but the state may say too bad landlord, you lose. 2) Assuming your attorney (Or you if you’re able to decode the laws that relate to your situation and are willing to go to court in front of a judge against a “sick” kid.) think you have the right to collect the rent I’d give them two options. 

As long as I do not lose money I think I'll be ok with that.

You will lose the capital gains exclusion by doing that.