The paperwork sort of selling yourself is the VERY EASIEST part.

I don't know if today's climate of the city recognizing a need for more housing might make some sort of small difference (something you'd have to discuss with them) but, other than that, this is an accident waiting to happen.

They will have all sorts of resources to help you. 

Check with a couple lenders that do these sort of loans.

We NEVER go for land than DD to sort if it will work, that would waste monumental amounts of time. 

Zoning ordinances, building codes, and ADU rules are all hyper local, so I would suggest you get an architect involved to help sort through everything.

They are some sort of bot that positively talks about a product, seminar, or guru after negative criticism has been given. 

Do we do it through some sort of PM?

I haven't heard of that sort of agreement being commonplace.

Frivolous stuff where plaintiffs were looking to get onto some sort of public assistance forever based on a fall or a stumble where one should not have fallen or stumbled.