I will be investing roughly 10k into equipment for this new gig. 

The sale included a sound stage and all types of equipment.

I'd sell if I were you. 1) I don't like HOAs and certainly not for STR or MTR 2) the numbers don't make sense for you to invest in a big kitchen/bath renovation 3) it doesn't look like it's appreciating very well.

I have a DADU over my detached garage that my daughter used to live in, but now she is out on her own so if I want to do a more major renovation (need to refinish the floors and maybe open up the kitchen more), I can move into the DADU as well.

If the home is 100 yrs old, I'm assuming it's a definite gut which is going to require new plumbing, electrical, heating, cosmetics.I spent about $140K reno on my multi family in the heights on NY ave and there were massive problems with it but it was a gut to 3 units & adding 2 bathrooms, 3 brand new kitchens 4 bathroom reno in total, all new flooring, sheetrock , insulation, framing, doors, electrical, plumbing, paint, parts of roof etc.

Planning to start a complete home remodel (interior/exterior) on a home (currently 837 sq ft), kitchen and bathroom bump out, and add an additional bathroom. 

I have sold timber in years past and even had the sheriff seize equipment from someone illegally cutting it on my property.

You and this private person you met hammer out the details of the loan at the kitchen table so to speak and you seal it with a handshake and your reputation that this Private Person already respects or whomever introduced has vouched for you.But if a man opens a lending company tomorrow with 50 Million of his own capital and he checks in on the HML market to see what it bears and he copies his products and UW guidelines and now is he PML or HML? 

Start with a rental that has modest rehab requirements such as updating kitchens and bathrooms and make sure you qualify for permanent financing through a lending source that offers interest rates similar to that of  a bank.

Aside from not paying any rent since July, claiming she lost her 2 jobs due to COVID19 (and the California eviction ban protecting her) she's been complaining that there's a gap in the kitchen floor where flies could fly in, and black mold in the shower.