My favorite sims, approximately in order are Puresim, since it gives, what I think is about the most realistic career mode simulations. FPS Baseball was probably next and if it had continued development past FPS BB98, it might well still be at the top of the heap. Earl Weaver Baseball was an excellent game for its time, though a little hard to run career modes and heck, last time I ran it was probably on a 286 machine, I think..... Strat-o-matic was never my favorite, but I never played the computer version - the board game just took too long to run a season, though for its time 30 years ago, it was about the only game in town....
Diamond Mind was always a game I enjoyed managing a game in. Action PC is the same way, although it's never been programmed very stably. APBA Baseball for Windows was a blast to play in its heyday, and had the most flexible team and player creation system I've seen in a long time. But right now, to my mind, Puresim is a perfect storm of baseball simulation goodness.
Personally I think Puresim is THE best for fantasy and factual Baseball Simming of career type play - as mentioned in this thread OOTP has become WAY too detailed to be playable and enjoyable. I also play and love the Strat Computer game for season replaying as it is probably about the best to feel you are "there" seeing the ball flight and the various PBP and has the very best reporting and newspaper style reports etc. However I tend towards Diamond Mind as the best for strict replaying and most accurate overall by a small margin, but it is a shame that it misses so much out on the basic graphic side of a game....its all in the mind. Action has had a lot of issues but is very quickly becoming much more stable overall and with its graphics is better than Diamond Mind but less "accurate" if thats the word perhaps. I had and tried BBW and have to say that with its antiquated modular style of getting the game to run I was not that impressed but did have Sports Development Studios Pennant Fever with all its seasons. THAT had a play call speech and was what BBW should have been in my view - currently not available but will be again in 2008 with an improved and better simulation I understand. Also got Dombrovs Baseball which I believe is Statis pro computerised and thats a good game but obviously behind the others I have mentioned. Each game has its own area of expertise - at the end of the day its up to what the purchaser wants :-) And there are others I can name such as FREEWARE Strategic Baseball Simulator for the CC which is superb,...........
What I like/dislike about each (and I'll try to be concise...something very difficult for me LOL):
Strat - Good: charm of the ever-familiar card/board engine, nice auto-draft/auto-play options; Bad: copy-protection is a hassle, particularly for those who go back and forth between desktop and laptops
DMB - Good: great for leagues, flexible CM; Bad: no visible engine/mechanics, 'black box', attitude of game company towards non-online gamers
PureSim - Good: fun for endless experimentation and scenarios, fun "toy"; Bad: actual gameplay still not smooth, too much tweaking/updates/patching, historical replay mode feels like an afterthought
ActionPC - Good: easy to set up, easy to play, nice gameflow, good AI GM for drafting & roster mgmt; Bad: some questionable ratings (editable), a few too many mistakes on season disks (again, user-correctable)
I enjoy all of these games, as well as Baseball Mogul and OOTP. PureSim, for me, hits the sweet spot in the middle of the overkill (too much detail) of OOTP and the lack of depth of BM.