In general, it usually takes the first two or three months of the season to understand what an NHL club is going to give you for the rest of the year. By Christmas there have been losing streaks, winning streaks, bad games, great games, and everything in between. You know how the team's power play functions, how the blueline works together, what any given forwards' role is, and the weaknesses that should be tweaked before the deadline.
There will still be surprises of course, and injuries can always throw a wrench into future plans. But if you're looking for a day when you can say "This is what the team is more or less about", December 25th is a good place to get started.
The playoffs are always wonderful-- there is nothing like an NHL postseason in all of sports, and it's the part of the year we all look forward to the most. The downside is that emotional investment is at an all-time high; your emotions start rocking up and down like the stock market last week. An 82 game investment spread out over six months is a large part of the reason why the postseason is so great. It is also a large part of the reason why it is absolute torture. Shifts are scythes that slash through your soul.
The first month of the year is always the purest for me from an enjoyment level. You rediscover your routines from last season, add some new ones to the repertoire, and fall in love with the game all over again. It is exactly like being in a long-distance relationship and getting the chance to reunite once again-- all of the little things that bug you about her don't really matter for the first month back because you put it all in perspective and realize that what you love most is just how great it is to be around her all the time. You put up with the losses ("The Notebook on a Saturday night? Again?") and late game blown leads ("I'm sorry that took you out of the mood so quickly, but really, how difficult do bra straps have to be?") because that wasn't what got you into it all in the first place. It was the passion, the energy, the excitement of the sport. That's what the first month of the season is all about.
Which is why this breaks my heart every single time:
Just a little taste to remind you why you were hooked. Goddamn.