With all due respect, I don't think that is how this will play out. I don't think JR is going to sell the team before he dies. Maybe at some point if his health and cognitive skills fail him badly per Alzheimer or Dementia, he might turn it over to his son Michael.
Even if JR was still alive and changed his mind to sell, he does not have the luxury to have a sit-down meeting with each billionaire who bids trying to determine their ownership philosophies. Plus once there is an accepted bid, the other 23 of 29 owners have to approve the sale. They are not making decisions to accommodate Jerry. Jerry might have had some influence many years ago, but I don't think he has the respect or support of most owners today...especially after the dumb comments he made about how many of the owners are so dumb and Jerry couldn't believe how they were ever able to buy a team.
Plus, based on how much the Sox will be sold for, there won't be any billionaire bidders wanting to buy the Sox to just run it with ignorance and stupidity as Jerry has. Rich owners coming in today will want to win. The cost to buy a baseball team today is so exorbitant, that they will only spend that type of money because they have the money and they want a wining baseball team. Look at the last sale of the New York Mets with Cohen. Regardless whether he is a successful owner yet or not is irrelevant. The fact is, Cohen wants to win at all costs and is willing to spend ridiculous money as opposed to the loser Reinsdorf. With the huge valuations of teams today, that is how the new owner profile will look.
The day this Sox team is sold will be a very special and happy day in my life, as well as for tons of other loyal die-hard fans who have been blatantly screwed for too many years.