I feel the same way. I have played about a dozen game using dynamic difficulty, and I am at about HoF so it' s roughly what I feel I should be. I have not made a serious run for higher levels yet.
I wish the mode actually takes a bit more than OPS and run differential into account for demotion/promotion. Rookie through All-star was a breeze for me, but my approach kinda suffered because I was hacking with Power swing all the time to accelerate the promotion.
Ideally, I think the dynamic difficulty should consider standard performance as well as something deeper like plate discipline stats. Then I am actually more interested in some system that actually informs the gamer where he stands and how he could improve.
Also some way for the game to converge to the right difficulty level quicker, either by making the initial difficulty customizable or by doing binary search type of thing.
But some people who aren't as familiar with the game may still benefit from dynamic difficulty adjustment.

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