Snow tires, no problem, except I'd not want to swap out 6 tires seasonally.
Best tire value for ALL conditions, imo, is find your favorite HT/AT/MT depending how aggressive you want to go and have them siped.
On heavy trucks, just sipe the center tread rows, leave the outside rows alone to help with tire wear.
As far as trucks, yeah can o worms, but you're correct, lightly used diesels command almost as much as new. Many reasons, but around here, a big part of it is a lot pay retail price and then a few years later, taking their "loss" puts them close to the Dave smith, Dennis Dillon prices for new.
If looking used, here are the trucks I WOULDNT want, for various reasons.
Powerstroke, 03-14
Cummins, anything with a 4 speed auto trans up to 08
Cummins 07.5-09
Cummins 10-13 (only because it's the old chassis new body, 14-up are mo betta, frame brakes, suspension)
Duramax 07.5-10
Realize these are broad statements, but for an expensive last you forever truck with no mods or emissions deletes, I'd look past these.