Wow. I can't believe I missed this post when you started it. I am also an owner of a 66 Beetle and have been thinking of combining my love for overland and aircooled VWs for a little while now. When it comes to long distance travel, it's the only car I would really feel comfortable in. It's so simple to understand mechanically and the engine, although underpowered, is tough as nails. There's only so much that can go wrong and a small emergency kit will almost cover any situation. I've seen guys JB weld the engine case together and the thing run for months afterwards. Not to mention, for a regular passenger vehicle, they have great clearance and with the engine and transaxle centralized over the rear wheels, GREAT traction.
The 1966 model IMO is probably the best for travel. It was a one year only vehicle and it was made in the middle of the transition between the classic Beetle and the more modern version. It was the last year of the "classic" look Beetle but, you got a couple of great improvements for the model year like ball joint suspension, higher hp engine, and a vent for the front windshield defrost. So, still looks damn good and has the perfect mix of simplicity and a few modern improvements that only aid the vehicle.
My 66 has been stripped down from a restoration I started over a year ago. I had fell into the whole "slammed" trend and it really hurt the little car. I decided to strip it and found it hard to find the time to finish between work, school, and kids.
Here's of pic of it before I took it apart.
It's an original Sea Sand 66 and still has its OG engine and trans. I plan to restore it to a more stock form. There's been a feeling brewing in the basement of my mind and soul. Almost a sadness since I haven't driven the car in so long. This post really has inspired me to get back out into the garage and get on with it.
Quick question...You said early in this thread that the car had a 1200 in it? Was the original 1300 gone?
I have had a 1200, 1300, 1500, and a 1600DP in some different VWs I've owned. I can tell you this, the 1300 is the way to go. (Although, you can't go wrong with a 1500SP, or 1600SP or DP. That 1200 is for the birds. The 1200's cant even get out of their own way and, atleast for me, always were incredibly frustrating to drive because of the absolute lack of power.) The 1300 always had a low end grunt that the other engines didn't have and sounded kinda raspy at times like they were revving faster than they actually were. You might say they had a certain "fun factor".
For the OP and those inspired by this post, I suggest watching this video.
https://www.youtube.com/watch?v=SdjRhk6USR0 It features probably the first guy to ever overland a Beetle. It's a touching video and absolutely worth 27 minutes of your time.