Wholesale or Buy a property w/ a muddy title? Horror Story and ?

[Aaron Foster]

Property: 4 acre Lot with 3 houses (all under the same tax deed) In the DC Suburbs. 

Back Story: The current owner had this land in his family for bout 100-150 years. He did owner financing to a lady who had the property in an LLC about 9 years ago. She put the deposit down and made 3 payments a year since. This held the foreclosure at bay. She never paid the property taxes. Once she lost the court case she appealed and said the house was her primary residence (moved a family member in one of the houses put a mailbox with a lock on it). She then lost that appeal and filed Chapter 7 Bankruptcy to prolong the process. Lost that in the court systems and turned around to file Chapter 13.  After a few more appeals she finally lost but continues to file appeals that the court system keeps shutting down. The owner had the family member evicted and deeded back to his name an paid $70k in back owed taxes. 

Numbers: House #1 is rented for $1,000 (under market value),  House #2 is turn key - just needs millings/gravel driveway replaced and a few touch ups that should rent for approx. $1,400. House #3 was the eviction of the family member and needs renovated but will also rent for approx $1400. The property is already hard money approved. There is an additional acre of land that can be subdivided and sold off that was once part of the original farmland about 200 years ago. (Utilities at the street)

Obstacles: I had the first title company pull records (600 pages) who said their underwriter won't approve the deal for title insurance because of her appeal and court history. I had a similar response from another title company who stated they don't want to walk into a fight knowing she has such a appeal happy history. 

My deadline to close on the property is July 10th (Two weeks) and the owner said he has a cash buyer lined up. I'm friends with his sons and son in law which is why he's given me a few months to see this deal through but I'm running out of time. 

Questions: I'm still considering wholesaling this deal but would rather keep it as a very profitable rental. Any thoughts, insight, options?