Using a 5 year overall outlook all speculation.
1)*Calgary
2)*Toronto
3)*Winnepeg
4)*Vancouver
5)Montreal
6)Edmonton
7)Ottawa
*Playoffs minimum 3 out of 5 years
Calgary in the next 5 years imo will be the most successful, I have them in the playoffs each one of those years. This year they have an opportunity for a very deep run and if so the following 2 years after won't be much of a stretch to do the same. Top Players will still be in their primes and the veterans (Gio, Backlund, Hamonic)will be properly replaced with young pieces Valimaki, Hanifin, Dube. Calgary has a history of making moves and signings to strengthen their weak spots(better or worse) I took this as a factor.
Toronto will be an interesting case. They really need to answer some questions in the next few years, will they overspend on their youth? Will they acquire a #1 defensemen? Can Freddy stay consistent? They have the offense to propel them into the offseason every year. It will be very difficult to surpass and compete with Tampa, Washington, Boston, Pittsburgh hell even the Islanders the next few years and when the windows close on some(Pitts,wash,Bos{temporary closure}) they have to deal with other teams on the rise like Buffalo. The east is strong with youth and poise, Toronto has the youth part in spades.
With Winnepeg, health and growth need to be consistent. In 5 years they have a lot of aging core pieces in Buff, Wheeler, little and Myers who could be retired or gone via Ufa. Hellebuyck, Schieffle and Trouba will be entering their 30' s and the youth of Morrisey, Laine and Connor might not be enough to even make the playoffs in years 4 & 5. To top that off SJ, VGK, Cgy and Nashville will be their measuring stick these next 2 years and personally I don't see they them making it through any come post season.
Vancouver, a little bit of hommerism but going off some potential here. Big youth movement with lots of cap space. If they can find a way into the post season or just outside this year the next four will be built upon. Agruably will have one of the best 1-2 centre combo in Pettersson and Horvat to go along with a soon to be rocket candidate every year Boeser a top Defensive and Goalie prospect to be a mainstay for the next decade in Hughes and Demko they have the youth to open a new window while other West teams windows will be closing (SJ, Nash, WPG, VGK). Canucks next 2 years will be a learning curve and growth period years 3-5 they could be among the league's best.
The Canadiens will have to go through a few years of finding their identity. Weber and Price most likely gone in a few years and Gallagher, Petrey, Tatar potentially also gonegone leadership will have to come from somewhere else. They have a great outlook with some top prospects and youth in the pipeline but will be missing some core pieces now and into the future.
McDavid can only do so much, Edmonton needs to clean house and build a new leadership team if it's not obvious enough already. With some nice core prices of RNH, Draisltl, Larsson, Klefbom and youth in Bouchard, Nurse and Pulijjarvi they have the start of a nice team, but, are already well behind other West coast teams be it this year or over the next 5 years. Too many factors be it Trading woes, UFA signings and Drafting over these next 5 years might not be enough to catch the rest of the West.
The Sens look rough with no first round pick and a thin pipeline of prospects. No Karlsson and with Duchene, Ryan and Stone possibly following out the door. Can't expect a trade to recoup the lost assets. Could this be Andersons last season? Nothing to draw in big UFA's, Too many ?'s. Even in the scenario to sign everyone is the team even good enough to make the post season in 5 years? Probably not. Going forward it looks like only Tkchuk, Chabot and White are the only notable pieces, great players but too many holes everywhere else. Things can turn around quick to give a better outlook but even with that in mind in 5 years they may only have 1 season of success.