I was building some new construction a few years back on the Oregon coast.. and I got a framing bid on a 2200 sq ft house that was not complicated and I got one bid at 52k..

If the property doesn't sell there, then it proceeds to the judicial sale (free & clear sale) where liens etc are wiped clean.So, if someone buys a property just prior to the judicial (free & clear) sale, it is just a normal sale and other liens are NOT wiped clean.

And once you get past the sizzle, it's always more complicated and not quite so easy.

If they are in an annuity, that complicates things (high fees and possible penalties).

The exclusion should be available for a gift or for a sale but it can get complicated and there are certain steps and forms you will want to file. 

I think moving all of them could be complicated.

With something as complicated as insurance and as much money on the line, there should be a lot more transparency.

This may seem obvious now, but I have always operated under the assumption that the more complicated the deal the more risky. 

The story behind it is complicated, I discussed that on another post if you are interested. https://www.biggerpockets.com/forums/51/topics/741921-family-property-dispute?

Complicated and expensive enough that it's probably not worth it for $27K of repairs.3.