I am finally interviewing several contractors and GCs about starting work on a 3bd 2 ba in Long Beach, CA.  

Welcome to BP community, check out some of the local meetups we have in Broward listed on the events page, as well as several local REIAS.

I've been communicating with the gentleman for several weeks now, he's emailed me information on what he needs to qualify me for an FHA loan, however, I'm a little nervous because I live in Wisconsin.Has anyone ever worked with an FHA mortgage counselor/originator in another state?

I sold a house in December in 37208 and I had multiple cash offers in several days. 

I have several CPA contacts for Missouri.

., this may be difficult for several reasons. 

With that being said, do you guys think it's a good idea to purchase a Turn-Key multi-family property for well over the asking price, with the intentions to house-hack and also use the property as a rental income stream for the next several years ?     

He lived at home for several years, and wondered if he should buy something, in his case, a place to live in.

Well there are several reasons for this.

If that's the case, in the future you might do as @Amy Beth suggested and make it so all tenants are "jointly and severally liable" for the total rent.