[Syd Thrift]

If anything OOTP is probably more versatile when it comes to creating teams of all-time greats like that. You can bring in any player from any season (now including Negro Leaguers!) and put them in a league against each other. If you want to do a single-season replay you're going to want to turn off the development engine, although there too there's a way to play where you start your league in, say, 1901 and instead of having 1901 players you have players randomly selected from the history of the league so, like, your 1901 Giants might have Jim Eisenreich or Brian Downing on the team (of course you can also just do a "regular" replay).

I should add that all of the things that OOTP does to balance seasons, make the leagues work, etc. is algorithmic in nature and not hand-curated the way SOM seasons are. You also don't have to pay for each and every season, which makes the "all time" type leagues more feasible (I know SOM has pre-packaged "all time" leagues but if, say, you wanted like Mike Greenwell on your all-time Red Sox team because you were a big fan of Mike Greenwell, that's easier to accomplish in OOTP). I also think that the algorithms, frankly, tend to do almost as well / sometimes better than SOM, although there will certainly be differences of opinion as to how they work (for example, since this is a multi-season GM sim, guys with one year monster blip years like Roger Maris or Norm Cash will often come in with lower ratings even for 1-season recalc; personally I think this is exactly what should happen but people will disagree).