Feels like you don't have the right attitude to start a side gig. You're never going to go anywhere if you just throw your hands up at actually good ideas.

Especially food/ice cream trucks. Do you really belive it costs "easily over $1 million" for a license? I'm not from Montreal but feel free to show any proof of that number. I doubt it's that much. Whilst a truck is more expensive (Still probably less than $50,000 to start) A hot dog stand or simple food cart business can be started for less than $10,000. With $20,000 you could even pay someone to operate it for you while you work your day job. And in an urban area with lots of people around you would have a VERY hard time not being profitable on your initial investment within a few months of owning/operating a food cart. Obviously a big factor is how often you have the cart out but if you have the money to hire someone, it can be out much more than just on the weekends. Then on weekends all you have to take care of is making sure inventory/supplies are ordered, doing some basic accounting, and other misc management tasks.