Your situation is more complicated than typical scenarios i've read about , so does seem like a question for a CPA (who has good knowledge of real estate - sounds like plenty of CPAs don't know how to handle this).  

We are creatures of habit, and we often perceive change as a bad thing – we perceive it as risky, costly, or too complicated.

@Hannah Stern, The trust doesn't complicate anything. 

If you are new to real estate investing, buying your first property in a retirement account is do-able but makes things more complicated as there are extra steps you need to make sure you are 100% compliant.I would suggest making things simpler and investing in your own name and when you have more experience to experiment if its possible to invest with a retirement account.

Real estate does not need to be that difficult or complicated.

I'm thinking of starting an LLC but I have a question on whether it's better to start off as a partnership or solo.My brother and I have discussed starting up a real estate investment business, including fix/flips and rentals.Initially, I was thinking of starting off as a partnership LLC but the taxes may get complicated as would any potential disagreements on how to handle difficult decisions. 

However when it came to the portion where the discussion of attempting to transfer in other properties and refinancing any existing properties, it became *very* complicated and just looked like a whole tangled mess of legal fees and a jumble of paperwork involving land trusts, living trusts, etc.Then I thought to myself. 

Insurance is important because holding the wrong type of policy can result in denied claims.There would be further complications if these are both FHA loans.

They were great and handled a complicated issue for me.

This part really isn't complicated.