So I thought about it if I sell my Cherokee and combine the proceeds with the 1600 I was going to use to upgrade it in the first place I might be better served going out and buying a 4x4 Jeep from the get go. And I'm having a hard time picking a hole in that plan.
The problem needs to be framed properly. A "4x4 Jeep" leaves alot of holes. There is no doubt that 4wd is good around here, not so much that you cant go anywhere without it, but it opens up areas and options that are not smart with 2wd.
But what kind of jeep? Folks have alot invested in that issue and it may be difficult to get reasonable advice. IMO, the classic "wrangler/cj" jeep is too small for anything but daytrips, maybe with a passenger. Look around at all the roof/tire/bumper racks as folks try desperately to make room for enough gear to make it through a weekend. That starts to put you into trailer territory. The XJ is about the bare minimum to pack enough gear for more than 2-3 days. When they stopped production jeep was out of the market until they did the stretch wrangler (kinda) and finally the 4 door puts them back in that size market. Its still small but workable.
If the criteria is Jeep you have two options, XJ or whatever they call the 4 door model. Now look at the costs through that filter.
transfer case- $100, D30- $150, install maybe $200?