After they've bought a few single family rentals in their own name, and maybe deeded a couple into an LLC, and try to buy their first apartment building, they realize they need to restructure everything.

@Emily N.Emily, not sure where you sourced your capital, but is the 5 year hit negotiable for restructure?

I suspect we may have to sell off the single family portion of the portfolio to generate capital to pay down and restructure some of the MF loans so that we have enough cash flow to keep them afloat.

The mortgage restructuring simply tacked on payments to end of mortgage, so not making much sense there either.

There's a higher likelihood but it could also just mean the sponsor made a poor decision on the type of loan they put on the property and it could make sense to restructure the capital stack with a new loan and a capital call and/or preferred equity. 

We have our company restructured last year so I can provide some insights, I'm in Florida as well. 

he'll just need an addendum and all contract documents to state he has the ability to move in within the 60 days.The risk if it's tenant occupied is he might have to evict if he legally purchases and the tenant does not vacate.75 days move in wont work I'd stretch out the escrow by burning time till you're within 60 days or restructure the contract:

I want to build wealth in real estate; I've restructured my life to be able to learn and immediately apply and take risks.

Finish our last 6 unit renovations on current properties, pay down and restructure our renovation debt, and buy 20-40 more units (if my husband doesn't kill me ;) )

In fact if nothing else works, you might go to the bank and see if the lien holder will restructure the note.