In Louisiana, this process is typically much more lax and I know several people who have succeeded in having homestead exemptions on several properties at once (no idea whether it's legal). 

You are in California (and guessing the property is)...contact a lawyer that specializes in evictions. 

I guess what I'm looking for is a legal loan shark, do people like this exist?

Are any of these, or other areas you have thought of, areas close to those places or those people? 

Hello Damon,It's great to see Local (and Surrounding) people from H-Town in here.   

I have done exactly that while recommending contractors I have worked with that don't upcharge like crazy (unlike the people they sent) - let's see what their response is. 

A lot of people do this professionally, but make sure you vet the operator if you're considering it.

I’ve heard people say don’t do it, but not sure why and frankly don’t want to be dishonest if they ask.

Are they worth it… every year people waste money on car insurance, home insurance, and medical insurance….

The HOA funds are limited and if something happens, there will likely be a special assessment; roof and/or exterior paint are the big ticket items that are near end of life according to building assessment.