Start spending on that TD, keep it tip top! I would second the trailer hitch idea, nothing handier then a hitch. But be sure you get a hitch that attaches to more then just the bumper shocks, research the euro hitch for what I mean (it has nice arms into the chassis).
A/c in Canada is a tricky thing, few shops actually know how to do it right (my Dad's SD went through many compressors, court case and all-this was the dealer in Ottawa!). I would strongly suggest you find a well known a/c specialist and have them prepare an estimate first, it could get ugly really quick. There are some essential steps to converting to R134A (the only option up here) that cannot be overlooked for a long lasting system and it takes time to pull a good long vacuum that most shops refuse to do, they like quick and dirty.
I know exactly what you mean with the truck, I had the same machine-it was just too much truck and too tough on road trips suspension wise to be comfortable. I hope you got a nice sum for it, they held value really well.
Greg