Reported the bug and got into contact with a developer who said this problem had affected a few others too. We figured out what was causing the crashing and there will be a fix in the next patch. In the meantime, as long as I employ the workaround, I can play. With that said, here is a proper review of the game.
Interface: 8 out of 10. The user interface takes some time to get used to because there is a bewildering amount of features you can toggle. There is a very useful search box in the upper right hand corner allowing you to quickly look up any player or coach
in the history of the game. There are countless pages that can range from quite useless to indispensable. You can bookmark the ones you like for easy future access. Once you get used to the UI, playing the game becomes second nature but until then it can be quite frustrating trying to do something like changing the name of the Best Pitcher Award to the Cy Young Award. You can "shortlist" players or coaches and get updates every time they do something noteworthy.
Graphics: 1 out of 10. You really need to download and install the unofficial HFP 2010 All-In-One Add-on pack. Even with that, I would only rate the graphics at 3 out of 10. There are no animations of any kind. Those coming from baseball games found on the console aren't going to be happy. One positive, and this is a big positive for me, is that player's portraits are digitalized and change from year to year. So when Jason Heyward is inducted into the 2035 Hall of Fame, he'll look like a 45 year old.
Sound: 0 out of 10. There is sound, but you'll quickly turn it off because it's so annoying.
Gameplay: 10 out of 10. When they say, "play Play as either GM and/or coach of pretty much any professional team in any league from any time period. You really can do anything. When I say anything, we're not just talking about AL or NL, but also the PCL or Florida State League. Think you can do better than Brian Cashman? Start your game in 1998 as the GM of the Yankees but beware of dealing with Steinbrenner. Be careful about which time period you choose though. I would hate to lose that 5 star prospect because he got drafted to go fight the Nazis.

You could also create feeder leagues from Japan or Cuba or from college ball. I don't think you can run any of the teams from feeder leagues, but they can exist in your baseball universe if you want. I chose not to have feeder leagues since college players will still enter the draft and Japanese and Cuban players will still appear in free agency (though without proper stats). You could also create entirely fictional leagues if you choose.
As you can see, the attention to realism and detail is unsurpassed in baseball sims. Sabermetricians rejoice! There is no clutch rating. You can easily look up a player's .BABIP, FIP, or ERA+ stats. All pitchers have three main ratings which govern how well they strikeout, walk, or avoid giving up homeruns. Statistics are ridiculously accurate and players seemingly progress (or regress) accurately too. Rule 5 draft picks, supplemental draft picks, putting players on irrevocable waivers; it's all there. Injuries are frequent and are realistic too. Getting hit by a pitch or collisions on the base paths have a greater chance of producing injuries. Some players are just more injury prone than others. I once had a player injure himself in the offseason, walking through a glass window. But that happens sometimes if you have dumb players.
Speaking of dumb players, every player also has personality ratings. I was really excited when I saw Elijah Dukes on free agency, but after looking at his personality profile, I didn't want that cancer on my team. On the other side of the spectrum, there are players who may not be superstars, but are good influences on their teammates. New in OOTP 11 is a storyline engine where a player can undergo a series of events where you get updates as their story progresses. I like that it is there but as GM, I worry about having to deal with some kind of Tiger-esque drama in my clubhouse.
Another new feature is dynamic leagues. If you're playing a historical league, as you progress from season to season, new teams will be added, teams will re-locate, and league structures as well as rules will change. It could be historically accurate or not. Imagine if the Dodgers never left Brooklyn. Imagine them as part of the AL East. It could have happened! If you're starting a new league in 2010, who knows what path your dynamic league will take.
You can also play in online leagues against human opponents. If you can't get enough fantasy baseball, this is the next best thing.
About the only complaint about realism are how rainouts happen (or rather, never happen). While there are weather effects on a game, it is never enough to rain a game out. Just enough to delay the game causing the manager to go to the bullpen because the starter can't get it going again. I would love to see games rained out, forcing double-headers to be played.
Overall: 8 out of 10. This is text-based simulation at its finest. I am constantly amazed at how realistic the game is. If you're a baseball afficionado like me, you can find yourself wasting many hours on this game. For $40, the replayability and longevity of the game make it a great value. There are very few bugs and my experience of the game crashing is the exception, not the norm.
"Steal a little and they'll throw you in jail, steal a lot and they'll make you a king." - Bob Dylan