Unpopular opinion but I would as well, Ullmark may never have a higher value than he does this offseason - that said I bet they keep the tandem and try to get Sway on a bridge deal. Around 8 to 9 mil total for that tandem is a steal and a big strength moving forward.
Just in terms of asset management, the Bruins likely are better off shopping Ullmark at his absolute peak value this offseason. Vezina, record-setting seaosn, goals, fights, possible Conn Smythe? A playoff team or borderline team that's a goalie away from a run (LA, Seattle, possibly Colorado, Pittsburgh, etc.) will give up a lot for that. Swayman is an RFA and only worth what his compensation could be in an offer sheet, which is like two 2nd rounders maybe.
We're in cap jail and with Bergeron/Krejci likely retiring, the limited pipeline of centers, likelihood that Gryz/Hall among others will be traded and Clifton walking in free agency, I don't suspect the Bruins will be anywhere near favored to make a cup run in 2024 or 2025. But at that point they'll have expiring money, prospects like Lysell, Harrison, Poitras closer to breaking, etc. and they'll be able to rebuild around Pasta/McAvoy/Lindholm/Zacha. Jeremy Swayman could be under team control for that time and can be the starting goalie at that point. Ullmark is a UFA in 2 years, he can walk for nothing theoretically after two seasons in which we are not expecting to be contenders. It seems pretty open and shut to me who they should be shopping.
But I've been wrong about just about every move Don Sweeney's made the last few summers, so I guess we'll see how it all plays out.