The insights offered of popular players sticking around longer after their prime days are very accurate, imo, reflecting the discrepancy of older RL players compared to OOTP.
Though I hate the phrase "This happens wayyyy too often in OOTP..." but....
I just had Tim Keefe retire with 299 wins, and he did not suffer an injury. Yes, he was 46 yo, but in his last season he got 1 win in ZERO starts and 17 IP. IRL a team will give him a chance to hit the important milestone. In this same league I have Al Pratt retire without injury while sitting at 3999 strikeouts.
I was at Arlington Stadium opening night in 1989 to see a recently reacquired Bubby Bell collect his 2500th hit. BTW, Charlie Hough pitched a shutout that night.
Buddy Bell was through, and retired shortly thereafter with 2514 hits.
The Rangers were not expecting him to replace Steve Buechele, or realisticly thinking he would be a productive DH for them, but they brought him back for the milestone and the standing ovation of a sold out home opener.
Wade Boggs got a contract to play for Tampa Bay in order to get to 3000 hits.
A little coding tweek to give preference to players nearing important milestones would have a bit of an impact on more veterans sticking around later in their career. Having teams more willing to sign and play such players, and having the players more willing to take less pay to reach the milestone would be a realistic feature, imo.
Here it goes....I have seen players retire one hit, HR, win, K away from an important milestone WAYYYY too often in OOTP, and this needs to be fixed!
Important Milestones I would suggest giving preference to reaching are:
2000 Hits, and every 500 after
500 HRs and every 100 after
2000 Ks and every 500 after
200 wins and every 50 after
I also would have the same preference for players playing for less and teams more likely to sign and give playing time to players approaching league records in each of these categories.
I love OOTP, and I much appreciate any review and attempt to implement this suggestion by the OOTP team.