I’m also a Brewers lifer (which I’m sure most of us here are), and I disagree. To me it all comes down to expectations, even if they may be unrealistic.
Yes, the teams of the late 1990s/early 2000s were not very good (even terrible) but we expected that to be the case. Going to a game then was still entertaining because any day the offense could put up 10 runs so even though they lost A LOT, the games themselves were much more exciting.
Because of the change in ownership and the moves that the FO made, we became better and had a few successful seasons. We had some young players (primarily pitching) that gave us hope for some deep postseason runs going into the late 2010s/early 2020s. Obviously 2018 comes to mind when we had a really, really good team. This success raised expectations for the FO to improve the team to get us deep into the postseason a few more times while we had this young, talented pitching. To use the FO terminology, we expected them to make the moves to take BIG bites from the apple, but the FO did not make those moves and they seemed content to just hope things go well enough to be able to take a bite of the apple. They were partly right as the team has made the postseason four years in a row now, but outside of the 2019 season there was basically no realistic chance that they’d make a deep postseason run.
Even though the team has been winning games the last few seasons, they way they are built makes for very boring and disappointing games. Relying on the home run and not focusing on situational hitting has made them very hard to watch. Any given day they seem like they could be easily no-hit. Not being able to drive in runners causes the pitching to have to be perfect (and this isn’t the case this year) so our 2-1 leads quickly evaporate when we don’t get a hit for 5 innings.
All this being said, yes, the team is winning more now compared to 20 years ago, but they are playing a very boring style of baseball that is hard to watch, and they aren’t playing to the level that we’d have expected them to be playing at after the 2018 success. The window with the good pitching is essentially closed.