Choosing a first car, daily driver, for my son

[notstock71]

So the time is almost here for Zach to get his learners permit, 3 weeks to go. I am starting to look at options for his daily driver. We just moved so there is now 2 lane county highways to consider for him to get to school. Snow, drifting and ice has made me decide something 4wd is a necessity. I would love to find a clean 2dr Tahoe or Yukon, ZR2 S10 or Sonoma or a Silverado / Sierra. Ive been all over Craigslist and there is no shortage of vehicles in the sub 5k range. Anyone have opinions, advice to offer up? I'm not afraid of something in the 100k mile area if it has been taken care of. Rust is my biggest enemy here so I have accepted that I will have to travel to get anything.

If this is rust free I would be all over it but I haven't called yet plus getting an inspection is a new hurdle I have never had to tackle. It is a nice exams of what I'm thinking though.
https://chicago.craigslist.org/chc/cto/6073739721.html