As a former student myself, I’d prefer to live on the West side as well.My only concern about the West side is I feel that the student rental market is over saturated and would be worried about finding student renters each year.

Now I have contractor saying they would recommend repair of bath and kitchen and preference would be that tenant be gone. 

If the sale of the property was via a warranty deed, then a claim could be made by either you, or preferably the title insurer, against the seller.

You can also be very direct and upfront, depends on your style and how you prefer. 

He could get a preferred return for the use of capital.

Cody at the moment I'd prefer turn key and anything 2 units or above.

For the rest, it comes down to your preferences, but if it were me, I would cashout refi the duplex owned outright because debt is so cheap right now.

I think this would be based off of personal preference.

I would prefer to do it at closing to avoid the transfer tax associated with moving it into the LLC post closing 

Preferred rate is 7, supposed to be about 10-12 paid quarterly.