Best thing to do would be to get your core, keep them together, add to it through draft and trades, and never, ever commit term and dollars to replaceable players.
Greening and Zack Smith? 15 million dollar deals each for something that a UFA like Tyler Ennis could do for 900k. That's 26 extra million to play with over a 4 year period.
Nate Thompson? 3.5 million dollar deal that could be done for 750k from any prospect in the system or UFA. 2 million extra bucks over a 2 year period.
Alex Burrows? 5 million dollar deal that could be done for 750k by any prospect in the system or UFA. 3.5 million extra bucks over a 2 year period.
Derek Stepan? 2 million dollars that could be replaced by any 750k guy in our system. 1.25 extra million over the year.
Connor Brown and Chris Tierny should be phased out next season, would save the team 11 million the next 2 seasons, and could be replaced pretty adequately through a simple trade, short term signing or ELC. Neither guy is more than a replaceable role player, they should be treated as such. Nick Paul, should he be a guy we sign to a 3+ year deal worth 9 million, or would that money be best invested elsewhere? Zub is a guy that looks as though he should be a fixture on our right side, and with his little track record in the NHL, should be up for a 3/4 year extension < 3 million, a perfect deal for the Sens.
Rule of thumb should be spending less than 3% of the cap on guys who are not in your top 6 (with exceptions to guys like Pageau), and spending the bare minimum on guys who could be in.
Bloated UFA contracts, stay away unless able to get a very good player. Don't pay a premium for guys likely to decline ion the next year or two. End up with a Lucic, Ryan or Eriksson. A team in the financial hardship of the Sens can't deal with this.
Sign our core guys off their ELC's to 7/8 year deals. Ride them until they are 27/28, make a decision the summer before if they will resign. If a contract extension isn't signed in the summer prior to the seasons starting, start the bidding war, don't wait until the trade deadline.