What's the Messiest Title Situation You've Tackled, and How Did You Resolve It?

As the topic says, I’m interested in hearing about the trickiest title issues that investors have encountered and overcome in acquiring properties. Hoping we might learn from each other’s stories, and/or possibly get some entertainment along the way.

Going first, I still haven’t done that many deals yet, relatively speaking, but of those that I have closed, I think the most unique title situation was a seller who inherited a property from his father (titled in seller’s name only); however, the father stated in his will that while the seller would be the sole owner of the subject property, the seller had to allow his brother to live on the property, as long as the brother was alive, so I couldn’t get an insurable warranty deed until we produced documentation that the brother had in fact passed away several years ago. In this case, the title company accepted a copy of an obituary that had been published in a local paper at the time of the brother’s passing, and did not require a death certificate.

The reason I’m thinking about this topic currently, though, is because I’m having ongoing discussions with an interested seller, who I’ll call Robert Smith; however, the county records show the property owner as the equivalent of “William Jones Estate c/o Robert Smith.”

What Robert Smith has explained to me is that he received a quit claim deed to the property from his great-grandfather and great-grandmother, but the great-grandparents are not the last property owner on record per the county, “William Jones,” either. Rather, William Jones was the parent or grandparent of prospective seller’s great-grandparents who executed the quit claim deed.

So in effect, supposedly, the property has been passed down within a family for something like 4 or 5 generations, with an apparent break in the chain of title along the way. So I’m wondering what might be necessary to resolve this, such as a quiet title action or something more straight-forward / less costly, and also not sure of the likelihood that the prospective seller I’m talking with would ultimately come out as the only current owner, versus some other heirs appearing along the way. Property could likely be resold fairly quickly today for around $100k. I have not agreed to a price with the seller, yet, because I am trying to determine likelihood that this deal could actually close at all, and if so, how much cost I should factor in on my end to have the title cleaned up.