I lost my husband (and partner) late 2014, so I am also single mom (with the help of MY mom), now without a partner. 

Imagine if the 4th, 5th, and 6th deals double the money you lost in the first three.  

I used to have that attitude of not worrying what people thought about me, but somewhere along the years I lost that.

Lender has a collateral interest, they take the property, they have the right to sell for the amounts lost, as collateral and amounts pay off the bank, excess amounts are equity from THAT SALE.

I have lost many nights of sleep over the whole time I had this property.

If you are getting it at a cost elsewhere, (HELOC, or even at a lost opportunity elsewhere), you have to take that into consideration.You know the health of the company....go with your gut.Mike P.

And in general, how have you dealt with contractors who have "lost motivation" for whatever reason?

As soon as you closed you lost most of your leverage.

I've had a property manager end up costing me thousands and thousands of dollars in lost rent and property damage simply by failing to do their job and trying to take the easy route.

But, yes it would make sense that if you paid me an option fee to buy my property for a certain $ amount, for a set period of time, and then I wanted out of that agreement (for you to release me from the option agreement) before it expired, you would want your money back, and maybe some extra for the "lost opportunity".