1) Next offseason, chances are we still won't have cap room to do anything with him (resign, S+T for a player)
We're at around $50.9M right now for 10 players, which is roughly $14M or more under the luxury tax threshold for next year. Throw our pick in there, and we're around $11M under for 11 players. We would have the flexibility to match a reasonable offer.
2) Others will disagree, but I think free agency will open up next season and Ramon can get a pretty good deal that Hammond won't have the balls to match (or simply won't be able to).
Possibly, but we'd have more room and leverage to accept a S/T than we do this year, being only $1.6M under the tax. Next year we'd have room to match, which gives us more options.
3) It is unlikely that we can move him during the season (Do teams acquire his RFA rights, or is there a rule I am missing?)
Not sure on that one.
So while yes, only paying 1 million to retain a good player who will help your team next year is of course a no-brainer, I don't really see much long term value in this type of deal. I'd much rather see the Bucks place their cards on the table and offer him a 3 year deal at 3 per. "Overpaying," maybe. But if we got Sessions into that type of deal, especially when his value is at its lowest, we take a small risk to increase his future value, both as trade asset or as cheap player to have on the roster.
I think there is definitely value. You move his RFA status into a year where you have some flexibility, even if it is not much. Lots of teams have money next offseason, so his chances of getting an offer are higher, which increases the chances of a sign and trade.
There is no harm to taking him back one year at $1M with RFA status next year that I can see. Unless you think he makes the team worse over letting him walk and keeping Ridnour.