my manu/billups/holiday for another's wade/jennings
my millsap for another's jennings
I'm not sure what to expect from Jennings when he comes back from injury. It might take him a while to get going again, as they may be cautious with him (unless they are fighting for playoff seeding).
I would probably go for trade 1, depending on how Jennings does down the stretch. Wade should stay amazing. There is talk that SAS will rest Manu down the stretch for the play-offs once they secure seating. Billup's value might also fluctuate depending on the Melo trade (he might get packaged even though he doesn't want to be; if Denver falls far out of play-offs after the trade, he might get a timeshare with Ty to let Ty develop). Holiday should be about the same down the stretch. This trade will also depend on who is on waivers since it's a 3 for 2.
I would not do trade 2. I know Milsap had a rough stretch recently, but he was dealing with the thumb injury and should heat back up. That is too much to gamble for Jennings.
The bigger question is whether there are any stats you are after? I feel like trade 1 may be close to a wash in overall value, if the players remain consistent.