In general, you get to carry this paper "lost" until you sell the property and reconcile all of the income and expenses while you held the property and estimate any tax liability.  

The PM would have to carry a large bill or payments would have to be processed to them for the work upfront.

Ask for an advance from your boss, or borrow from their 401k, house, boat, etc.Talk to your kids teacher about it.Ask a hard money lender.Ask the seller to carry that much (or that much more.)Call Grandma.

There are a variety of unforeseen reasons you could be forced to carry your property and not have tenants and cash flow.

Good and bad - you're entering a property without the bad habits of previous tenants but are now faced with some carrying costs in the first 2-3 months to fill tenants, renovate, and stabilize property. 

If you were there when it happened your witness will carry a lot of weight.

This may not be a rule that can carry into every market, but when I see a condo that should sell around 75K selling for 50K I have generally found that it has a $250/mo HOA fee with it.

My sons job made a mistake on his SSN, one number off, the CPA carried forward that mistake,  I didn't check it. 

B) Carry over to the last month of the renewal term (which would now be May 2020)?

While a heloc might carry a higher interest rate, I prefer it to a cashout refi because if you don’t use it, you don’t pay anything.