The biggest problems for all Canadian NHL teams:
1. They don't win Stanley Cup any longer, this loosing culture among Canadian NHL teams has to stop. For many players it may feel like the end of their career going to a team always loosing? Toronto used to be devastating for young promising talents but now it looks way better, finally.
2. The pressure playing for a Canadian NHL team is huge and lot's of players can't handle it.
3. NHL teams in Canada lack of patience building for the future (maybe because of the huge pressure) and constantly make lots of stupid trades.
4. Financials may sporidically be an issue for some Canadian teams but not for teams like Toronto or Montreal (they can't use this as an excuse).
The situation looks way better this season though which is good, Canada and the NHL teams in Canada are increadibly important for the hockey world.
Also I think that Canadian teams should have Canadian team captains (in general), they need to take responsibility and not shy away. Look at Karlsson now in Ottawa where he is hinting that he may want to leave in the future, you can't talk like this as team captain for a Canadian team, it is a catastrophy when being a leader. A Swede may never feel the same kind of heart and passion for a Canadian team like a Canadian player do, there
may always be a difference.
I'm a Swede myself but I think Swedish players sometimes are overrated as captains for North American teams, this has confused me many times during the years. The only real pure Captain leadership talent (suitable for a North American team and mentality) I have seen to come out from Sweden is Landeskog. Landeskog became a team captain too early, yes but I still feel he has the capacity to become a great legendary captain, the next 10 years will tell.
I felt it was a huge mistake making Sundin a captain for the Leafs. Everybody could see this huge responsibility took a big negative impact on him and his play even though he never admit that himself. Sundin was way to calm, almost shy sometimes and laid back for being a NHL team captain if you ask me. The Swedish national team is different, he was perfect for that task.
Many of us Swedes (because of cultural differences etc) are a bit too shy, calm, not very outspoken, too soft in a group (sometimes a team captain need to get angry), not totally fluent in english etc. It's way better doing like Colorado with Forsberg leading by example instead of being forced to become a shy team timid captain as a 20 year old.
You guys have to understand that Sweden in many ways still is a socialist country even though we have a mixed economy with several huge privately owned coorporations (Tetra Pak, H&M, IKEA, Ericsson, Volvo etc). We believe in decisions with everybody agreeing, we believe in "consensus" decision making. Our cooperations usually have rather flat organisation structures, comparing to classical hierarchical structures. I'm just trying to explain that our mindset sometimes may be a bit different from a North American. ;-) We build fantastic strong teams but may sometimes have some leadership issues.
You also need to read the Swedish Law Of Jante to fully understand us. :-D
Law of Jante - Wikipedia