Sure adding the extra teams does make it harder than when it was just 4 on each side. But generally speaking, baseball playoffs are still the flukiest off all sports besides march madness. So yes, the added round did make it harder, but the nature of the playoffs themselves is a key as to why MKE actually has a chance every year they make it.
We're frustrated that as a consistently good team we keep losing so kind of looking at it from the normal big market perspective in that sense. But, the overall nature of MLB playoffs is what even gives the small market team like MKE a legit chance. So in a way its a chicken/egg or catch22. We have a chance because of the fluky system, but right now we're on the bad end of the fluky so we complain about it. This system is far superior to the past which would have had NYY/LAD as 50% of the playoff teams every year. The fluky and bloated system is what's giving us a chance, so we can't really get too mad at it(other than generally pushing for salary rules similar to NFL/NBA so things are even).
3/4 teams in the AL right now are KC, Det, Cle. And sure the Yanks will probably still win but in baseball no game is more than 60/40 at this stage so its not some foregone conclusion the others have no chance. If we keep getting there every year there will be a deep run eventually. There is really nothing structurally/strategically different they should be doing for us to be angry at or 'demand more' etc. You just have to keep rolling the dice. I'd say the strategic 1-2 year 'go for it' spending moves could be increased. But IMO they have been open to it when the situation presents it like it did with Moose/Grandal/Hoskins. So generally I think they do have that as part of the strategy like they should.