To their credit, a I noticed a few improvements had made on their dime (new exterior lights were installed and  motion sensored).

I have worked with him as much as possible, but his situation is not changing and his ability to pay is not improving.

I thought I might switch to paying off the properties I have (at least until the market improves some.)

If your mom, as the owner is living on the property, and it's converted to a triplex, she would not be subject to the rent control ordinance (assuming she has lived there for at least 2 years).Another option is to make improvements to the units, and then use the pass through for capital improvements to raise the rent on the tenant.

the idea of house hacking is that it allows you to invest in a piece of real estate, save money (with OO financing, or doing your own improvements), and have a place to live at the same time, then keep the property long term.To calculate a true return, you have to "pay rent" to your real estate investing account.

He had no financials on the place, but after an inspection and realizing i needed to put about 3k a unit into 3 units to improve their "showing appeal" I will be able to rent the 6 units for about 3600 total.

Expect for non-accredited investors to have more options over the next few years and for things to continue to improve over time.  

Its possible to greatly improve your credit in a few months to a few years.  

We work with a lender that works with low credit scores and educates you on how to improve them contact me and I can put you in touch with him.

Would the land need improvements to do this?