I'm not a huge fan of these short term leasebacks as you could have a serious problem on your hands if the sellers refused to move out. 

Madison has pretty strict short term rental rules if you don't live at the property, so mid term furnished rentals is a strategy I have seen done here. 

They will often voluntarily come up with increased security deposits, easily accept month-to-month rental contracts, and find other ways to work with you.

Lot's of people use the term UpState, and since I've got my BP alerts set up... it isn't solely used by New York Upstaters... apparently lots of different states like to throw around 'upstate'  Anyway, I digress.  

They can close in less than 2 weeks but without seeing the deal terms even if you are a stellar borrower they can’t fund guarantee they’ll lend.  

While this rarely happens, it allows the banks the opportunity to call your loan, claiming you've breached the terms of the loan agreement.

I have a 13 unit under contract for just under $1M and my agent is quoting me $4700/yr with $2500 deductible. 

What recommendations do you have in terms of what to take a look at/action items after 1 year? 

Now, this is not all agents/realtors, and that's why it's imperative to find someone who you trust and looks to build long-term relationships, and not someone just in it for the quick money, but it definitely was a chunk of them.

We installed a Carrier Furnace & Air Conditioner in a house that was under contract but not closed yet.