Your quote is isn't quite right. He didn't say a player thinks he is choosing the Sox, like he is decided. He said Manny is thinking about choosing the Sox, implying he hasn't decided but is contemplating it. Big difference.
I think its correct to say though, that if he signs with the Cubs, it will be at a discount. If the reports are true that he is waiting for the Cubs, we know he would like to play for them, it will depend on the creativity of the discount.
The player opt out are guaranteed money. If he plays well he opts out and gets more. If his play declines, he doesn't opt out and continues with the contract. It's a no lose situation for the players.
I don't think the teams really care if they don't have a clear picture of the roster 3 months before the season. How many teams are being held for ransom by this once in a lifetime situation (age/quality), 3 or 4. Not really a big deal anywhere else but in those places. Every other team could be signing and trading if they wanted to. They are just choosing a different direction.
I don't think this has anything to do with a deadline. These players will be signed prior to Spring training if anyone wants them. I think it has more to do with clubs fans being more tolerant to rebuilding than a deadline.
The worst thing to happen to the middle range FA was the Cubs and Houston showing that tanking and building from within is really the better option if you don't have a 250 mil payroll. The teams sucked for 4 to 5 years but the fans came back.