It saddens me to see you feeling this way towards our current team and management. I'm probably too young to understand all your sentiments, but I get your point.
I became a Milan fan in 2001 the moment I saw Shevchenko, blazing through opponents' defensive lines, for the first time.
Since then, the most bitter I've ever felt was Istanbul 2005. Initially, I seriously considered quitting being a Milan fan, or even a football fan altogether. Of course, that sentiment didn't last long, but that's just how bitter I felt in the moment.
The most hopeless I've ever felt, though, was probably during Pippo Inzaghi's tenure amidst our banter era. We ended that season 10th (!) after our only summer transfers were loaning Cerci, Destro, and Bocchetti, and acquiring Menez as a free agent. Back then, even after selling off Balotelli for 20M to Liverpool, we couldn't spend one single Euro.
Our team was as mediocre as it could get; it weakened by the years, and we lacked the funds to strengthen it. And then there was Pippo, the next ex-legend in line to get his legacy burned, downgraded to being Silvios pet, and Silvio himself of course who couldn't care less about the club since his political career was basically over. Nothing suggested that anything could change anytime soon - which is exactly what happened. That's been the low point for me as a fan.
The last couple of years haven't always been easy. But reliving the enthusiasm of the sleeping giant finally awakening and first getting back into the CL, then winning the least expected Scudetto in its history, and to then see the first CL Semifinal since 2007 has been a hell of a ride.
The last 12ish months weren't always as good as hoped, and losses like yesterday hurt me just as much as the next one. And I'm not looking forward to seeing Inter possibly celebrating their 2nd star against us in a derby of all games.
Nevertheless, that feeling of never-ending disappointment and depressing hopelessness of 2015 is luckily only a far cry today. I'm thrilled for the next couple of years; the same management that gets a lot of beating these days ensured we've positioned ourselves superbly well to collect the fruits seeded in all those past years, both in terms of sporting and financial stability. There are some crucial decisions to be taken in the next few weeks and months, sure, but I'm very excited to see our next moves.
I personally have rarely felt as passionate and proud to be a Milan fan like these years, probably only rivaled by the early 2000s when I first became one. 2007 already felt like the painful end of something big that dragged on for many years in hindsight, culminating in one last hurrah in 2012 that ended as swiftly as it happened. Everything after that has been pure agony, not the slightest comparable to our current setbacks.
But yeah, that's how I feel. Of course, not everyone will agree with me.