The all star one is 5 not six. 300 steals isn't bad because my players speed is a 98 and his acceleration is a 97. 2000 hits really isn't that bad. I have like 11 or 12 more seasons I can play you can only play 15 correct?
You should be able to at 90, but you will likely have to play an additional season or two until you get all the career milestones only being a 90. You CANNOT avoid the key games, especially when you're in an MVP hunt. You can get traded to a shitty team and avoid the playoff impacted games, but regardless, you'll play about the same amount. Annoying, yes, I know. I would just swing for the fences every time to try to get the 300HRs ASAP. You get the .290/6season, .800OPS/6seasons, 2MVPS and 6 allstar appearances and then you get to decide which other one is quickest. The 300HRs was for me.
What about simming to get all of the Career milestones? Is there an easier way to avoid playing all of the key games? Would it help if I requested a trade to the Pirates/bad team? My player is a 90 overall so I should be able to just sim the rest of the way right?