I obviously need to look back over our purchase documents, but I remember when we purchased the house there were several rules we had to abide by (we had to owner-occupy the house, for one, and there were some big tax penalties if we wanted to sell within 10 years). 2.

I am under contract on an occupied rental.

Below are images from an actual apartment that's been occupied by the same tenant for almost 30 years.

FHA will lend on a 1-4 unit where you live in one of the units, making it an owner-occupied, which is an FHA requirement. 

I think getting into the multi-family space is an excellent move whether you plan on occupying one of the units or not.To know if this is a good move in your particular market, I'd consult with a lender and a local Realtor.

My previous insurance company doesn't write policies for these anymore.Which companies will write a policy for an occupied property that I don't have access to yet?

If I wanted to build an owner occupied 4-plex on land which I could subdivide and build multiple units (4-plexes) would I be able to live in a unit for 1-2 years, refinance to a conventional loan, and apply for another FHA loan with 3.5% down to build a second 4-Plex to live in for another year or two?

I was hoping to put as little down as possible, and then refinance into an owner-occupied conventional loan once it's built.

Looking to take advantage of an FHA and owner-occupy for a year.2) Network locally (Chicago or NWI)3) Find multi-units to BRRRR and manage personally.That's about it for right now! 

Looking to take advantage of an FHA and owner-occupy for a year.2) Network locally (Chicago or NWI)3) Find multi-units to BRRRR and manage personally.That's about it for right now!