way2roll,
I'll be watching this thread closely as I've had similar thoughts. I have similar plans upon retiring, though for me that's probably 3-5 years away (I hope). So far, I've done all of the maintenance on our gasser, including chassis work, except for the 2 recall issues on the W-22.
I'd like a DP once I retire. While it's several years off, I have pretty much decided that I will be looking for a high-end rig, probably around 15-20 years old which is in the $60-$100k range. Rigs that probably cost $500k & up when new. I want them old enough to 1.) be in my price range and 2.) NOT have tons of wifi/bluetooth/touch panel controlled/monitored appliances on board. I like physical knobs & switches!!! LOL I also want to make sure I have at least $10k in reserve should I run into a major issue while on the road.
So far, the searching has been fun and doesn't cost anything. :)
Are you thinking about getting a brand new rig or a newer used unit?
Good Luck,
~Rick