I agree with the most part of your assessment.
In regards to goaltending: both Price & Halak will be looking at getting similar deals during the off-season, likely in the $4 million+ range unless there are no offers for their services, which i really doubt would happen. If Toskala could get such a deal when he joined Toronto, there is a market for young top-notch goalies with unfulfilled potential like Halak & Price. This means that looking at the way their current cap is set up, the Habs would have room for only one of those two. And even if they would have room, Halak would never want to remain in Mtl just to play back-up again, likely accepting an offer to play for another team or join the KHL. Same with Price, he'll want a guarantee that he's the starting goaltender & don't be surprised of teams like Detroit & Toronto don't make a pitch for his services, whether by trade or a straight-up offer, no matter what the cost in compensation.
Considering the future free agents the team will have once the season ends, and if the cap space doesn't increase, the Habs will have about $11 million to sign 9 players. Among those 9 players will be Plekanec, Price & Halak. They will very likely re-sign either Price or Halak, so i can't see Plekanec re-signing with them since they'll have no money left to sign the other 7 roster spots. As you are aware of, Metropolit, Mara & Bergeron will be free agents & the Habs likely would like to retain at least 2 of those 3 players, but at a bargain price. This would leave them room to sign a couple of 2nd or 3rd rate free agents, but there's no guarantee that the cap won't decrease instead of increasing, but i don't see this happening.
As you're aware of, what's gutting the cap space are the large contracts given out to Cammalleri, Gionta & Gomez. These contracts are long-term & won't disappear from the books anytime soon. Even though overpaid, at least Cammalleri & Gionta have earned their keeps. Sure, Cammalleri has a lot of trouble scoring at home & Gionta has been injured for quite some time, but at least they make something happen when they're on the ice. Gomez has been an enigma, but rumours that he can't play in a pressure-cooker like in NYC & Mtl might turn out to be true. As of today, he's only had one 20-plus goals season, a few years ago when he was with New Jersey. His goal totals in each of the other seasons were all under 20 goals per season. He's a good passer, but of course, he's not getting paid $8 million per season to just pass the puck. He's paid to lead & score goals, and he's doing neither. He's also a 'white elephant' on the cap space, since he's unmoveable due to is poor production & top 5 overral NHL contract. No one would dare touch him in the league, and even if there was a sucker out there, that team likely wouldn't have the cap space.
There's also the case of Andrei Markov becoming a free agent after the 2010-11 season. Gainey better find a way to sign him to an extension, or else he'll have to fork out more money for his services come 2011. A player like Markov would likely expect to receive Jay Bouwemeester-like numbers due to his value with his current team. Would he accept a discount to play in Mtl? Likely not, since there's always the chance he'd like to play in his home country for the KHL. So the Habs will be stuck with an interesting problem in regards to what to do with Markov, who's also a fan favorite. But the team has shown in the past that fan favorites don't matter by simply looking at the way they've dealt with Kovalev & Koivu.
Now, what to do with the current goaltending situation? If he's not getting the bulk of games, Halak & his agent have expressed a wish to get traded elsewhere where his services would be more appreciated. But who says Carey Price doesn't want the same thing? There currently isn't much of a market for goaltending & teams paying the price to obtain any of those two would likely want them to sign a contract as soon as the deal is made. I see the Habs moving a goalie & Plekanec prior to the trade deadline, as early as February.
