Ric Flair met with Vince McMahon on 9/20 at Titan Towers, and according to the Wrestling Observer Newsletter, the meeting didn’t go well. McMahon was upset that Flair brought lawyers with him. There are unsolved issues which nobody appears to be aware of. The meeting resulted in the two sides being farther apart.
Flair owes the company a significant amount of money. McMahon extended Flair a sizeable personal loan to help the "Nature Boy" resolve his tax problems with the IRS.
In terms of creative, RAW head writer Brian Gewirtz is against the push of Flair beating top guys on his way out at his age since he would be leaving the squared circle.