This is a rough view on how I'd go about it based on play up to this point.
Re-sign
Bernier - $5.25m
Kadri - $4.25m - $4.75m
Winnik - $2.5m
Panik - QO @ $771,750k
These are the 4 main re-signings that I'd like to happen. I have Panik at his QO, But it's possible that it could be higher if he get more of an opportunity as the season goes. Winnik is very valuable on the PK and can give you solid 3rd line minutes. Kadri and Bernier are two guys who should be part of "the core" going forward IMO. Kadri has taken massive steps in his play without the puck this year; And Bernier is without a doubt the #1 and has made our goaltending the most stable it's been in a decade; 24 and 26 years of age respectively as well.
If there's enough room.
Santorelli - $3.5m - $4m
Franson - $3.75m - $4.25m
Holzer - $1m - $1.5m
While Both Santorelli and Franson have had impressive seasons thus far, I consider them both to be luxury signings at this point. Both are UFA's in contract a year and will be looking for multi-year deals I'm not sure we can do at this point. Holzer if he continues playing well is I'd like to keep, and may make some someone with a higher cap hit movable. I think it's important to have room for younger player(Nylander, Percy, Leivo, 3D Swedes) to make the club, So re-signing every one for next season isn't something I'd commit to anyway.
Trades(who's movable)
As of now we have just over $16m to spend for next years team for about 8-10 players, Pending how many we carry. After the players who I think are important to sign(first group) we'll have around 2m-3m to spend(not counting the estimated 3m cap growth) on 4-6 players.
So 3 obvious players to move out to make room, And 1 not so obvious
Lupul - $5.25m AAV
Gardiner - $4.050m AAV
Polak - $2.950m AAV
Reimer - $2.3m AAV
Tons of speculation about Lupul and Gardiner already, It seems likely that one of them at least won't be here even at the deadline perhaps. Both should net a good return with some form of a cap hit, But it should be move that opens up space. Polak isn't a deal that will happen, But at nearly $3m if some like Holzer or even Granberg/Nilsson can emerge next year it's another way to create cap room. For Reimer, They would probably like to move him before the deadline if they can.