I've always checked off the F box in legal documents, and I've never got in trouble for it. *shurgs* My drivers and Birth Certificate still say M, sadly (surgery will fix that), but my government health care card says Female and my SIN (Social Insurance Number) says that I'm also Female (not on the card, sadly, but the records were changed to say Female -- technically not supposed to happen until surgery, but the office didn't know what to do or the rules, so they put down Female as my gender). So, oddly enough, legally I'm seen as both genders, since all of those documents are legal identifying documents according to the government.
I know a few people who have been able to change their licence. Alberta requires the actual SRS, but if you hit the right office and convince them that the M is a clerical error, they'll fix it for you thinking it's a mistake. Although, technically, that's fraud and you can go to jail for that, but I don't know of any trans person who's gone to jail for it. Also, other provinces, like BC, allow you to change your gender on your licence without surgery, but just a doctors note. Canada Passport also lets you change your gender with a doctors note stating that you are a transexual and living full time as your target gender.
I think if someone did get charged, it wouldn't get too far in court 'cause they'd have to prove that, one, the person changed their gender in order to commit some major fraud scheme. Two, the case for us is that province is completly inconsistently with their gender marker rules (ie, AB health requirements vs Licence requirements -- AB health doesn't require SRS, just a letter.). Third, other provinces have different rules and you can argue that province A has such and such a right, so province B should, and federally the rule are different. So, yeah, it would be a silly case.
I know that there's been talk about challenging the current rules, but I don't know of any one who's actually got people together and a lawyer to do that. They'd also have to prove to the court that the incorrect gender marker makes a significant impact in damages (ie, can't find a job, discrimination, etc, etc). So, for a class action, they'd have to actually gather people and evidence. It's a long process. And also, you'd have to prove that the ID causes the discrimination, and not they way you look, etc. *shrugs*
In my case, despite the wrong gender being on my licence, I haven't any issues because of it.
--natalie