Hey folks, let me start off by saying a few things.
One, I hope I don't sound like a troll, just a Rangers fan that lives with two Islanders fans, is friends with a lot more, goes to Islanders games regularly, and witnesses first hand how the team-and their fans-suffer each year.
Second, I am not fully in tune with the Islanders budget, so if any of my ideas appear impossible, please let me know.
Third, I am a strong believer that the Islanders can be a playoff team in the next 1-2 seasons if they handle their transactions right. Big if, though.
Anyway, here I go. Here is how I would fix the Islanders and turn them into a playoff team soon enough.
Make a strong decision on Mark Streit- I personally change my opinion on Streit quite often. If the Islanders believe they can be a playoff team in the next 1-3 seasons they should keep Streit for not only his defensive play, but also for veteran leadership. If they believe they need to rebuild, there is absolutely no purpose in keeping Streit, and they would be better served trading Streit. I lean towards keeping Streit as of now, only because my plan would help the Islanders make the playoffs sooner rather than later. If the Islanders need cap room, trade Mark Streit immediately. Hate to say it, but he makes the most sense to trade given his age.
Find the Coach of the Present AND Future- You know better than I do if Jack Capuano is that coach, but no more changing coaches often. Whoever the Islanders coach in 2012 is should be the coach for the future. No hesitation.
Sign a Free Agent Goalie- There are two RFA's I'd look at, and two UFA's I'd look at. Courtesy of Capgeek, I'd try to sign or trade for Tuukka Rask or Cory Schneider of the RFA's. Perhaps, given that both of their teams have goalies, they could be had for less than market value. As for the UFA's, I'd try to sign Josh Harding, Brian Elliot, or Jonas Gustavsson. All three are young, and could cost a small enough amount for the Isles to get them. Use them to compete with/sort of mentor Poulin, even if that means letting Montoya go.
Find a way to get a Top Defenseman- There are enough UFA's where the Islanders should be able to get at least one defenseman this off-season. Remember, the Islanders could trade Mark Streit if they have to free room, but a Streit-led package for a top defenseman simply does NOT make sense, as no team would trade for an older version of the player they are dealing. Find an old defenseman that actually could have a good season, and provide toughness and leadership. Think Steve Staois but much better.
Draft an NHL Ready Defenseman- Regardless of the possible signing, I'd go defense in the draft over goalie/offense. Look at how Adam Larsson and Michael Del Zotto are helping the Devils and Rangers, and look at how the Islanders could use that help.
Find the Sneaky Value Players- Big goal for any team. There are always those FA that sneak through the cracks and end up having big seasons for relatively little $. P.A. Parentau was one the Islanders picked up themselves. One of those can go a long way.
Ditch the Oldies- Don't bring back Staios, Rolston, any of the old guys that slow down the team and take alternate captains spots. I already explained how to get veteran leadership, but rather than signing players specifically for that, sign players that would count that as a bonus to their skills.
Get rid of the Alternate Jerseys- I'm sorry, but those are horrawful. (Horrible+awful)
Fix These Stats, Keep this in Mind- (from an earlier comment of mine)
-Have least goals scored in NHL
-Fourth worst differential in NHL
When it comes to specific players the question has to be players value vs. value of acquired players.
Look for trades for everyone, see what you could get, answer the question, make the choice.
Anyway, I think if the team is built correctly around Tavares/Moulson/Okposo/Grabner it can be successful sooner than later. Let me know if I'm insane or genius or in between.
Best of luck, and if you do become successful stay away from the Rangers!