Sale 7 properties (some with liens/ some without) to the same person at the same time.Place all left over proceeds with the proper 1031 agent ( closing attorney).Use all the left-over proceeds as a down-payment for a much larger complex (will be identified prior to sale).

  $780,000 would be my maximum price as the cash that you would be left to pay back your down payment financiers at that price would be about $9000 annually. 

@Michael Babin with the limited numbers you have given you will only lose $104 per month. how I calculated it. 50% expense= $2025 per month  left over for PI. [email protected]% = $2129.

Also, I would want a lot of retainage left that he will get only on 100% completion.Am I being realistic here?

Totally agree with you on the Medicaid side of things, the goal would be to avoid it completely and cover the cost of care out with cashflow, SSI and supplementing from what is left in her retirement accounts or out of my personal funds depending on which route makes the most sense.

How many years are left on the mortgage?  

The house will be left to my wife when he passes.

Next, if there are proceeds left the sponsor gets a split of the excess portion. 

In your guys' experience, is this something that can be left to the buyer, or it is better if we pay for the repair ourselves before listing the house?

I always have to call the help line and have them walk me through it.. there is a reason once the NMLS system came in that huge numbers of originators left or went to work were they did not need NMLS> so yes the license Is NOT easy to get .. and you have to be a mortgage banker like me to write your own deals.