We don't even need all of that to go right to make it to the finals, IMO. Ideally we avoid the Bruins in the playoffs, that is basically it.
Look at the Rangers. They had a borderline catastrophic start to the year last year. New coach awkwardness, Lundqvist was hurt and not usually playing very well when he was playing, lots of contract rumours surrounding Girardi and Callahan, traded their captain away, etc. but they peaked at the perfect time, everything came together for them. If you have the pieces you just have to hope you're almost 100% healthy and have a decent amount of momentum come April.
For example, I'd say our 2012 team deserved a better fate than a 4-1 first round exit. Still had a fairly well rounded team, and they took the Cup champs to game 7 OT the following year without Stuart and Lidstrom. The team lost a ton of steam at the end of the regular season, and it was pretty obvious. I went from feeling like the team had an honest chance to go deep and maybe even win it all to doubting our chances in roughly the span of a week.
So basically, I really like our chances if our best players are healthy and have good line chemistry in March and April, and in a perfect world we don't play Boston in round 1.