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). 

Negative cash flow is not something I’d be okay with, but I know there are some instances where people are okay with taking a small hit for a big pay off with the appreciation (and hopes that the rent will go up).

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

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….

Personally, I'm not a fan, but I could see why some people like it. 

BP has been vital in making connections to learn not only with national people but with local investors in my area as well (no specific meetups though).