It was a great ride up until 2010/2011 when the injuries started.
Even at full health, the repeated playoff bounces have really taken the wind out of the enjoyment when in reality we're looking at the best NHL player since Lemieux. At the end of the dreadful '05 season, pundits put the Pens towards the top of the power-ranking list with the firing of FGMCP and hiring of FGMRS. RS did a bang-up job of getting the pieces needed to build the 09 cup team; leading from guys like Dominic Moore, to Ruutu to Rupp and others.
Our playoff performances in '07, '08 and then ultimately '09 were stellar. The team learned early on what it took to win, getting trounced by the Senators then coming back stronger advancing to the finals the very next season. That was quite a leap as typically teams work their way from Semifinals > Conference Finals or Cup Finals, so we were a bit spoiled in that regard. To everyone's surprise, a seemingly inferior paper team managed to capture the 09 cup with key pieces. I still remember Ty Conklin coming and playing lights out when Fleury was injured. What a shocker.
Sid's injuries and added frustrations definitely were the low point of the last few seasons. He seems to be back to 100%, with the Hart and Art Ross trophies, etc, but who knows. He didn't look right during the playoffs at all, or after the Olympic Break.
After Sid made it back, Bylsmalogic started to wear on everyone year by year. Calling for an HC change last off-season was the right thing to do. FGMRS really screwed himself by believing in Bylsma (this probably had more to do with the Jack Adams award + olympic selection which he ultimately blundered). Had RS made the right move during the summer of 2013, he'd probably still be here drafting defensemen.
So this year, of course the Pens do fine in the regular season trouncing teams like Florida, Carolina, etc, then losing to better teams that are built for endurance. The East is the weak conference, so numbers here are inflated. The epic collapse of this post-season finally saw change, but I don't think it's going to be for the better. I expect some frustration this year from Sid as everything is sort of "back to square 1," with trying to build a contender. The staff changes haven't helped either, and will probably see us teetering in the middle of the top 8.