1031 Exchange / House Hacking

[Kory Quitter]

I currently own and live in a single-family house that I paid $40k for. I am looking to "house hack" aka live-in rehab in a home I am currently in the works of obtaining through seller financing, since it is non-FHA compatible at this point. My plan is after closing on the new property, I would immediately move into it, making rehabs and getting it to FHA standards while I rent out the house I currently live in. While I am "house hacking" the new single-family, I would like to rent out the house I would be moving out of. Once the new house is up to FHA standards, I plan on refinancing to an FHA loan. After refinancing, I would like to remove the tenants from my old residence and make necessary repairs and improvements, and I believe a conservative sale price would be in the range of 50-55k. At this point I would like to take advantage of a 1031 exchange, and reinvest this into a multifamily property (2-4 unit).

How long do I have to rent out the old single-family before it is eligible for a 1031 exchange?

To my understanding, a single-family and multifamily (2-4 units) are fairly similar as far as traditional financing.  Is it possible to do a 1031 exchange from a single-family to a small multifamily?

If I am unable to utilize a 1031 to obtain a multifamily, is it possible to get an FHA loan on a multifamily, and owner-occupy one of the units? Therefore negating the 1031 benefits, meanwhile gaining the ability to put a down-payment on a multifamily.

Any thoughts or knowledge will be valued and appreciated, excited to join the biggerpockets community!