I subscribe to the Tom Benjamin theory of winning the Stanley Cup. The only real way to do it, especially in the salary cap era, is to make sure your team can compete for it every year and then hope for the best.
Edit: One other point I wanted to make is that making the second round 3 out of 4 years is a GOOD thing. It shows that this team actually is as good as we think it is. How many other teams can say the same thing? Three: Detroit, San Jose and Pittsburgh...two cup winners and a perennial Western Conference leader. That's pretty good company.
Randomness and chance have a lot more to do with success in hockey than people would like to think. It gets even worse in a group of 7-game series when suddenly a team can get hot and go on a Cinderella run (I'm looking at you Montreal).
The best that a GM can hope for is to get a collection of players who can shift the odds a bit in his favour, such that when the team gets lucky it wins a lot. For example...look at this year: The biggest difference between the Hawks and Canucks? They were healthy, we were not. They didn't have any injuries to key players. By the end, we had lost Mitchell, Salo, Edler and Kesler, effectively. Yes some of them played hurt, but when you play at an elite level anything that impacts your performance is going to drop you to non-elite.
Similarly a few years ago the Sedin twins got major illness issues during the Anaheim series. I'm fairly certain that the Hawks were fairly healthy last year too, but we had lost Salo and Demo.
The great thing about this team is that the core of our good players are ALL coming back next year. The Sedins, Luongo, Samuelson, Burrows, Kesler, Salo and Edler are back. MayRay will get signed. We have two or three good young forwards coming up the pipe (which is another key to winning in the cap era...underpaid skill players).
All we really need to do is to shore up the defense. I'm not sure how much of that can be done via free agency, but we do have some good prospects on forward (one could argue we're over-heavy on skill in the forward positions now) to deal for good defensemen.
But the fact is that Gillis has stacked the deck with good players and they're locked up for the most part for the next 4-5 years. The Canucks really don't have any competition anymore for the division title, at least for the next year or two I think, so we'll be playoff bound at the least and 3+ seeded at best. This is an excellent position to be in long-term.
We just have to hope for some luck one of these years. But I'd much rather be in our position than Calgary's, Minny's or Edmonton.