Everyone, these replies have been helpful and most appreciated. As I'm still climbing the learning curve I'd appreciate any additional opinions on narrowing my search to vehicle and era. For context, a little more background on my ownership profile:
On the old VW I do ALL work. I've dropped the engine to replace fuel lines and I'm currently putting finishing touches on a complete interior replacement (reupholstered seats, etc).
The VW is basically stock, the previous owner did bore it out slightly during a rebuild but as far as maintenance and care goes, it's just like it always was. And stock tends to be my preference.
I drive the VW in all conditions. We do our camping in national forests, traveling service roads. These are my favorite too. I've even "off-roaded" it with water up to the doors. But I don't have a taste for rock crawling.
On my modern vehicles I do all my own work except when I get pinched for time. In that case I have an independent shop I go to.
In the past I have tended to own vehicles with long production runs like a Suburban. More specifically, I think in terms of shopping owners and engines as I tend to buy used and engines with long production runs become legendary for a reason.
I was reading one of Scott Brady's builds and he said something to the effect of having a preference for "pinnacle vehicles" that have EFI and 70 mph stability. I agree with this statement but among LRs I'm not exactly sure where that puts me in a search as I am still unfamiliar with what is available here in the southeastern US. I'm in Atlanta.
And that reminds me of one final note; since I'm in Atlanta A/C would be nice. Last summer my son and I had a national forest trip planned and the temp was 99 degrees, in Friday afternoon stop and go traffic. We were supposed to take the VW but opted for the Suburban instead due to the heat. We were bummed about that. (Still had an awesome weekend in the Nantahala though)