I used to play Diamond Mind Baseball for years, but once OOTP came along that was the end of my DMB days.
The challenge and excitement of constructing and deconstructing a team as GM and manager with so much realism to the point where you can lose your job is something that no other baseball simulation whether it be a board game or computer game can offer.
IMHO, Diamond Mind started going downhill after Tom Tippett left the company to work for the Boston Red Sox. I used to love doing season replays back then, but got burned out on DMB not long after that and actually went back to Strat on the computer and board game. I still think Strat-O-Matic is the best baseball board game I've ever played. When I was younger I also played Statis-Pro Baseball which I enjoyed and APBA which is good although neither of them beats Strat.
I also tried playing Pursue The Pennant many years after I first saw the brochure and it's a good game, but I can see now why it didn't do as well as they would have liked it to: too advanced. Don't get me wrong, the developers did a fantastic job of making it as realistic as possible, but the board game was frustrating at times because most of the time consisted of looking at charts. A computer simulated game based on PTP called Dynasty League Baseball came out a few years later and it's good, but again, NOTHING beats OOTP.
If I could compare OOTP to any game, I'd say it's the baseball version of "Sim City". The same can be said for FHM as well.