When you add that: "The downpayment and closing costs would be one large hurdle"; I can't tell if you can only afford to do this once (thus tying up whatever you have saved) or multiple times.  

My biggest hurdle is we are going to buy 600-800 properties this year and I want to be the #1 buyer.

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People appreciate the balance of affordability and livability.What’s been the biggest hurdle for Orlando in pushing these types of projects forward?

An LLC doesn't make a difference in your federal taxes or what you can deduct.What you want to do is technically possible, but there are several hurdles. 

I've had a couple OOS investors ask about ADU potential in our market... not sure what hurdles there might be with the city (permitting, zoning, or otherwise).

The first hurdle was convincing them to leave via cash for keys.

What should I expect in terms of timelines, paperwork, or other administrative hurdles?

Would this hit your return hurdles?

I think the 2 biggest hurdles are finding the right team to do the work, given you won't be there to monitor it 1st hand.