There's any number of reasons why a game can crash, ranging from settings conflicting with each other (with all the options this complicated game has, it's going to happen every once in a while), to a user changing/modifying files or using alt-ctrl-del to cancel a game they don't like (which can corrupt a league file), to a power outage which corrupts the file. Eventually, something's going to happen - and there's nothing anyone can do about it.
I know, "the developers should make sure nothing conflicts or make it crash-proof". Easy to say... extremely hard to do, considering how complicated this game is. Sometimes, Markus and Andreas fix one bug... and as an unintended consequence, create another. It's frustrating and a never-ending cycle. (Besides, I've yet to meet a game that has NEVER crashed or had bugs...)
I suggest monthly backups (which is what I do), and the odd times I've had a corrupted file, I've been able to restore to an earlier date and play through with no problems.
Yeah, it's frustrating, but what can you do about it? Nothing.

If you get frustrated, walk away for a few days, and then come back to it once you've calmed down. That helps for any problem. Yes, I know, you feel you shouldn't have to, but reality being what it is... what else can you do?
Here's an idea that might help you: after you get everything set up the way you want it, before you play any games, save the game as a template, and then sim for one or two years to make sure everything works the way it is supposed to. Once that's done, if there's no problem, then you can play it out game by game. At the very least, if a problem develops, then it'll be easier to pinpoint it.
As for customer support, some of the options someone suggested just aren't workable. OOTPD cannot afford to hire a full-time staff to handle support, even with cheap labor. (Do you really want someone from India who knows nothing about baseball or the game giving you advice based on a knowledgebase article? I sure as heck don't! I want a fan, someone who knows the game at least a little bit, trying to help.)
At last count, we have a grand total of 4, just 4, people who regularly help out with support tickets. We have no Mac techs, and I don't think have anyone who knows the ins and outs of the new online league system very well (we're still working out a bunch of bugs on that, and some of them will be addressed in the next patch).
Throw in the fact that if we don't know how to handle the presented problem... we sure aren't going to take the ticket, because that will just make things worse. Consider also that if Markus and Andreas had to handle support, they wouldn't have a whole lot of time to fix bugs and code features, and then where would the game be without the new features people demand for every version?
Guys, we're trying. As I've said before, if you don't get an answer to your ticket in 3-4 days.. politely bump it by responding to the e-mail you received when you filed it, and we'll do the best we can. We're not ignoring you on purpose - this ain't EA, after all.