Normally I would recommend the LLC for a rental property, however, I would check to see if your current Insurance carrier will cover LLC's.  

I've been told that my personal insurance carrier would not add this 12-unit to an personal umbrella insurance, so apparently I need to look at commercial umbrella insurance?  

Moving into a new owner occupied right after purchasing an owner occupied will create a red flag for the underwriter.

If they cannot answer these questions that could be a red flag to either dig deeper thru references or keep searching- What to Look for in a Property Management Company I would look up NARPM and start with them...make sure their business model aligns with yoursBe relationship not transactionalits a people businessQuestions to Ask prospective management companies What are your average days on market for vacant homes?

I actually allow dogs, so this obvious lie set up a huge red flag for me.

Your attorney can help you out.A quit claim seems to be a red flag.  

However, it might be best, to ensure you structure everything correctly and avoid any possible uncertainties or pitfalls, to give any one of the experts a call because there are some moving parts and I find in a situation like yours, you are are going to need someone well credentialed in accounting/law/finance to plan this transaction in such a way that you avoid red flags when filing your return.

You should also get to know the postal carriers as they are among the first to know when a house goes vacant or someone moves.

@Chris McDonald - ok, so I have some red flags going up right now.You state your expenses, but don't list maintenance or CapEx savings.

The concern with Pool and the HOA is the biggest flags for me.