I do not feel any higher level of despair than at some times in the past. At the end of the Bryden era the players were not getting paid on time, the local high tech economy was falling down, and no one in town had the money to take on the team. It was 50/50 if it was going to move.
I personally am not over reacting to the current situation. IMHO the team has been going downhill for a few years. People like to point out we were a goal from the stanley cup finals last year as a reason to make the team look good. But in all honestly I think we just had a good run (all teams have those) at the most opportune time. The truth is we barely squeaked into the playoffs, we had the only negative goal differential of playoff teams, and we were the 2nd oldest team in the league. Many pundits questioned whether Ottawa would even make the playoffs this year. There has been the smell of rebuild here for 18 months, it just come to fruition.
Also we have to realize that the management aspect that is contributing greatly to the demise of the fan confidence in the team has been building for 18 months, and likely would have been more front and center if not for the run in the playoffs. the team picture taken at the start of the 2016/17 season featured an executive row that were all gone within 8 months A complete turnover. It probably would have been a more noticeable issue if the team had missed the playoffs. But the churn kept going on, and is still ongoing today. To me the negativity on management/ownership that should have been building for 18 months seems to have been condensed into several months, making the drop off in confidence appear much more steep than it probably should have been.
As for losing Karlsson, if the indications are from him to management (and we cannot know this) that he will not be resigning in Ottawa, then now is the time to trade him. It is just prudent asset management. It could be as simple as Karlsson saying he will not resign for any less than 10M, and the team does not want to pay it. It does not even have to be a money issue. To be honest there is no way I am signing this guy to an 10M 8 year deal. Aside from the fact he would be 37 when the deal is over, for this year he has not been playing like a 10M dollar D man. In fact far less. He has been terrible defensively to the point his additions on offense hardly make up for it. We are not a better team if he leaves, obviously, but can any team afford to saddle themselves to a contract like that for a player who may be a shadow of his former self? If we cannot win with Karlsson for the next few years when at least maybe we can get equal value for his contract, and his contract becomes a boat anchor when the rebuild starts to look good, it could all be for naught. Mind you the flip side is trading Karlsson will alienate so many fans that attendance will likely drop so bad there would be concerns about the future. Maybe if management would have been up front and explained the situation like the Rangers did the fans may be a bit more appreciative, but they have not.
So no I do not feel the lowest I have ever felt. But there is quite some time for this to play out, and the next 18 months are likely to be worse, not better.