A prior-year recharacterization occurs when the recharacterization takes place in the year after the year for which the contribution was made.

Identify  the asset (real estate) and imagine a timeline of events the occur in the lives of the record owners, creditors, PR's and heirs.So, in the case of a property that's changed ownership due to probate distribution, aka "inherited," the PR's job is done concerning this property once it's been transferred out of the Decedent's estate, whether sold to a 3rd party by deed, foreclosed on by a secured lender, or transferred to heir or beneficiary.While you might market to the distributee to purchase their newly inherited property, it would seem to me that soliciting the PR (executor or administrator) would be like asking a ship's captain to board after the ship has sailed. 

Or even if it is the millenials that bring it or just the millenials that made up the largest portion of the populace when the changes occurred.

When your LLC buys the house subject to, then a sale occurs.  

I recently learned of a Wholesaler meet up that occurred yesterday in Arlington, Texas.

While the loan underlying this investment offering remains in default, the following updates have occurred in the last 30 days.

It acts kind of like an insurance, and there is obviously a point where it would have made more sense to pay the treatment out of pocket when it occurred (like 10 years down the road).

Have anything and everything in writing, print out all convos, write down all dates and any issues that have occurred.

I don't think that your question can be easily answered without the leverage/cash discussion occurring. 

I actually hear this type of situation occurring very often where you have a property but are unable to move it.