There is definitely alot of organized crime in Montreal, but a lot of money is invested into fixing the water distribution system, which is crumbling and was neglected for decades. They usually fix 1-2 blocks at the time, and it costs hundreds of millions.
Roads do get a beating because of snow. Montreal definitely get more than Toronto, and the road system is way over capacity, with the number of cars and trucks increasing 2% each year.
The costs estimates are interesting too, because the construction industry is/was colliding in order to hike prices. So now all projects are fixed-price, meaning that companies won't take risks and tripple their estimates.
Some say that these problems started in the 60s, but got worse during government downsizing attempts. Internal expertise was lost and they had to rely on (corrupt) private companies. Others say that the restructuring were required to get rid of inside corruption. Whenever two government entities get merged, it's pretty much always as an attempt to water down corruption.
All that said, these days the city is pretty lean. I know lots of folks working there. I also did my small part to help liberate the city from Oracle consultants (siphoning the city) and also ran for borough office some time ago.
Just don't get your car towed. They are as bad in Montreal as everywhere else. And the city needs more public transport.