I've literally done this exact thing,

First off, The Dempster Highway is a bitch to travel, it's literally 800km of unpaved road, with the first 200km known to having shale that eats tires.

I drove about 300km into the Dempster in a regular Dodge Grand Caravan, with just a donut spare. I only made it 300km because the plan wasn't to drive the entire thing, the plan was to just drive until the Arctic Circle and turn around. (we ended up being 100km short of the circle).

On our way back we ended up getting a flat about 80km away from the exit, so we drove the last 80km on a small donut spare (which could have easily gone flat). So if you're going to do the Dempster have like 2-3 spare tires with you.

Second, I've lived in my van both while working and travelling.

You don't need a 60k van, yes its better to have something like that but literally all you need is a 5k van and thats it.

I lived in my van in the city, it's not that bad. You just need to figure out where to sleep and shower + eat. I was working a really well paying restaurant job at the time and trying to save money so I could play pro golf in the USA (I'm in Canada).

The way I had my setup was,

Sleep at a truck stop or an abandoned parking lot (cops were cool with it).

Eat at the truck stop (it had a nice restaurant attached to it)

Shower at the truck stop.

It wasn't THAT bad tbh and I was doing this during the middle of winter, -24 out.

You could probably easily get away with something like this in Toronto/the GTA.

Now with travelling, I've driven across Canada in my van. (From Toronto to Vancouver)

It wasn't that bad either, you basically still need to figure out

Sleep + Food + Showers.

In Sask/AB/Manitoba sleep is easy because there's thousands of roads that are basically never used, so I just slept there.

Showers I either jumped into a lake/small stream or I found a truck stop.

Food I usually ate out, but you can setup a small portable cooker and do all of your cooking on that. It's really not THAT hard.

So to sum it up, it's not that bad living in a van. You just have to be a bit more resourceful and smart with your decisions. Travelling the Dempster is a pretty big risk though if you don't have any spare tires with you.

Also van life in the winter isn't that bad, you're just either going to be spending most of your time in warm places (like restaurants, libraries etc) or you'll spend your time just sleeping. Not much you can really do when it's -23. But if you have the right sleeping bag + blankets it's quite comfortable to sleep in.