But they do all work to some degree.

and it does not look like the right deal for me and my investing objectives.However, this is the first multi-unit I have seriously looked at and want to make sure I am making some of the correct assumptions; which are below.

I would like to rent out my SFH that is conventional while obtaining a multi-plex (up to 4 units) with FHA financing.

Ive meet one other guy who owns a multi family complex and we talk all the time.

That said, I'm assuming that purchasing (and living in) a multi-family unit may be beneficial due to first-time homebuyer tax credits?

Flips, rentals, multi-family. 

The total amount of the loan would be about $575,000, which is less than the median average of single and smaller multi-families in this town.

So they will just see your program as higher rent than advertised.

Right now, I don’t have a lot of cash, but I am looking to get financing on multis, single, or raw land zoned for r2 and above near the theme parks, winter garden, Davenport, Kissimmee, no more than 160-180k I also am looking for referrals to property managers for when I do acquire more, as well as legit handy men/ contractors.

But, since you asked, here are a few items to be very aware of when you're reviewing your insurance program:Matching the property to the correct type of policy: Every type of property (single family, 1-4 multi-family, 5+ unit multi-family, vacant, rehab, commercial, etc.