I have a Tacoma with a pop up (wedge) camper, a Superpacific. It's been awesome, but might not be the best for ski camping if you do that a lot. Pop up campers are notoriously poorly insulated. SP does have an insulation kit you can buy for the upper tent, but I imagine it would still be cold. A diesel heater with the insulation would make it more manageable. I've camped in my SP down to about 20F and it's not bad with plenty of blankets or a warm bag. But that is just occasional use and it's still not awesome to hang out in from sundown to bedtime.
That is what I bought it for though, but typical Socal conditions aren't usually that cold. It definitely is better to hang out in though when temps at night are cold and it's windy, and it gets dark at 5pm - which is exactly when it sucks hanging out outside. Before buying the SP I would usually sleep in a bivy next to the truck - not great for hanging out in. So the camper is a lot better for sure.
It's a tradeoff for sure. If you do a lot of winter camping a van might be the better option. If you drive a lot of rough roads the rest of the year the Taco + pop up camper is worth considering. The SP and others like GFC (including needed options) aren't cheap though.

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