I watch a lot of documentaries, and a lot of sports documentaries, but I don't think there's nearly enough of a story there to sustain anything close to a compelling film.
Obviously, The Habs winning another Cup by the end of your dark years would be a perfect ending. Up to 1993, The Habs had never gone more than 7 years without winning a Cup! 22 years later, we're still waiting for the next one, the elusive 25th…
I don't see the full pertinence of your proposed time frame and wonder if it doesn't have more to do with access you might have to principals that were there at that time. The start is logical because it is near enough to our last Cup in 1993 and right around the first in a series of three lockouts. In '92, the players had striked for a greater control in marketing rights and the share of playoff revenue more than doubled for the players (from 3.2 Million to 7.5 Million). From the '94-'95 lockout, owners began making a case for an unhealthy financial picture in the NHL that required a solution.
The end of the time period covered by your proposed documentary is supposed to be tantamount to the end of the 'dark years'. Why did the dark years end at that precise moment? What was the turning point? What exactly changed? Who was instrumental in bringing this change about? Where's the evidence? What exactly qualifies as "dark years" a period that goes from day 'x' to day 'y'? Are we exaggerating the time frame? Are we not going far enough?
For starters, you need to define what makes for the 'dark years' and be credible in that definition. Those years should be the worst years to qualify and make that period as notorious as it sounds. If the audience buys the 'dark years', they will follow the story. At least, initially.
As another poster suggested, you need backstory (the success of one of the most storied sports franchises in the world, a spoiled but knowledgeable fan base, etc.) to demonstrate the tragedy of the arrival of the "dark years" and, perhaps, help show what had gone wrong in mismanagement during the "dark years". It can perhaps later be used as a comparison to show how current management may be returning to a successful style of the past.
I am really fond of the image you suggested in one of your posts. Celebration and ceremony from the dynasty years could be followed by a flame at Center ice that is blown out, leaving a trail of black smoke to signal the arrival of the dark years. The end of the dark years could show some of the modern opening day ceremonies that herald the past glory, wow the imagination, and give hope for the future.
Professional sports sell hope. As much as we like to claim that we can appreciate a good show, if our home team is assured to miss the playoffs before the season even starts, you can start counting the empty seats. A majority of seats may already have been bought as season tickets but, even companies will have trouble finding takers for their freebies...
You need some compelling hope for the future at the end of your documentary, something that clearly demonstrates a transition back to the light. Otherwise, it's tantamount to saying, "Didn't The Habs really suck from this day to that day!? They're not that bad nowadays but, Man they were bad…" It falls a bit flat and the audience would feel cheated to have followed the odyssey of the "dark years".
Even without winning another Cup since '93, if we had recently made it to the finals (like PITT under Therrien) and were stacked with one of the youngest teams that was brimming with incredible talent, then there'd be a compelling case for hope going forward; the team that is on the brink of coming into it's own and leaving it's mark on the league once it has finally matured!. A comparison of budding young stars from the present to heralded heroes from our dynasty years would make the documentary come full circle and sell the hope.
If you take the 7 year window between Stanley Cups (at it's worst before '93), there had been legitimate chances of winning one that were disappointing losses. Since then, we haven't really come close and that persists beyond the end point of your dark years. I'm wondering what the turning point out of the "dark years" really is? When and how does the light start filtering through and begin to chase away heavy clouds of despair?
Where is the Eldorado we are searching for as a fan base? Is it close? Was the end of the "dark years" just the beginning of a long, trudging step as the organization could finally gasp for air or a renewed hope for a return to past glory? Perhaps future glory will take on a different look than past glory because the league has changed, players have changed and society has changed. If so, what might that future glory look like? What does our road towards it look like. Are we, as an organization, on our way?
That's where your end point of the "dark years" becomes more dubious. Whatever the resolution to your story is, there is plenty of years following the "dark years" to potentially invalidate or, at least, diminish the impact of your message. Better to end the "dark years" closer to the present day to make the better future more credible. Outside of diehard fans, few can honestly say that they have been constantly elated by the Habs' performances since the proposed end to your "dark years" (2004 or so).
There's definitely something riveting to be done. Perhaps with a little help from Bergevin, the resolution to your documentary can come to life. You need to define your story to make it more engaging…
Good luck.