There were at least 5 problems with the dynamic pricing - caveat that most of this happened while was on hiatus from WIS and I may have the details not quite right:
1.) As mentioned above, lumping all leagues in together rather than just considering OLs. 1920-21 Ruth did not need a price increase.
2.) Not re-setting the counter after each increase. I think this was the big flaw. Once Joss was adjusted the first time, they should have reset his counter of "number of times used" to 0. They didn't, so he and others (89 HoJo...) got the max increase like every time.
3.) They didn't appropriately balance the increases with the decreases. Their method required the total salary in the database be equal. A relatively small number of players got big increases...a huge number of players got negligibly small decreases. So while a bunch of players immediately became unusable in OLs, there was no counterbalancing influx of players who were now better values.
4.) There was no need to increase the salaries of 200K players. Who cares if 200K Hughie Jennings was on a lot of teams because he provided a lot of PA. He sucked, and there was no need to raise his salary. Basically there are no 200K players from pre-2016 in the database anymore.
5.) They allowed salaries to differ for the same player. Like 1902 Bernhard, who now has different salaries for his CLE combined and his PHA combined versions, which makes no sense.
Basically they took a decent idea and botched it thoroughly.