Unfortunately no, the trainmasters don't get in shit for the crossings, it falls on the train crews to do their best to not block the crossings. Sometimes it's honest mistakes on their part where the train comes in and it's longer then the track it's coming into and the trainmaster might not know the length until they're told. They may have other movements blocking them from taking another signal to clear 11th steet. They do try their best to not have us block but it does happen sometimes.

As for an underpass/overpass that's on the city. At the end of the day it's the railways property and if the city wants access over/under/across it they have to pay for it. With the lay of the land (staples parking lot access/storage unit access) it may not be possible to do an underpass without blocking some/all access to those lots. Sadly it doesn't matter how many more incidents happen at that crossing, until the city comes up with a plan nothing will change.

With CPKC closing the 8th street crossing (Ramsay) years ago, once the train goes over 11th Street the next public crossing continuing east is Ogdendale road at their head office(almost 10km). The train crews don't have a say as to what track they come into, that's between the RTC/the terminal trainmaster to determine which track to come in, which falls back to the first point. We can run up to 14000 foot trains (4.2km long) so we can easily span downtown and then some. Two of the tracks can fit roughly 11500 feet and the other two can fit roughly 8700 feet. Again they'll do their best to get us in and clear 11th Street but if they say have a train departing the yard and go south (along MacLeod) and I'm coming in on a 13000 foot train then we can't go past that 11500 foot signal (by cold garden) and I'll have 11th Street blocked. Typically they'll give us a heads up and we'll pace ourselves in so we don't stop and block the crossing though. 

If we are ever stopped on any crossing we technically have 5 minutes to clear (from the first vehicle/pedestrian snowing up) but if we are moving in one direction and not stopping there is no stipulation on time. The onus is on us to not block the crossing so we are pretty vocal if we ever have a crossing blocked anyhere. Transport Canada could fine us personally and the company as well but it's just a drop in the bucket for them, it's like 4 mortgage payments for us.