Chris Mason, the primary adviser for a client's decision to put all their assets into an LLC is their attorney, not their CPA, and if my client, based on recommendations from his or her attorney, decides to structure his or her business in a certain way, I'm going to prepare their tax returns consistently with the tax code and in such a way that reflects the legal reality of their situation, not what a lender or any other service provider wants me to do.That being said, I think it would be wise for attorneys to understand the tax as well as lending ramifications of structuring a client's business in a certain way and should definitely connect with their client's CPA and lender before making recommendations.

My strategy for now is to pay a little extra in insurance premiums to cover liability up to 1 million on each structure.

.- Advantage of conventional is the lower MI costs and the ability to structure the loan with no monthly MI like Zak mentioned, however he did not state the break even where conventional is better than FHA.

Before buying I would definitely check out all the permits issued and inspections that would have occurred for the slab, electrical, plumbing and structural/foundation. 

I don't understand the legal structure of the place, why isn't it condos?

Not afraid of doing the work other than structural, electrical and major plumbing.

Is the roof structure AT ALL compromised?

Any business no matter how structured can write off almost any legitimate expense.

I'm the guy who's coming up with loan structures and terms for each building while my partner goes and execute it.

I believe the conclusion is that I do not have to update the stairs as per current code unless I am making any structural changes to the property as part of renovation.