With the first tax return in USA I bought 1986 CJ7 with 70 000 miles on it - June 1998 - and used it to commute to work on 95 and Capital Beltway in DC. What a dumb move, but I got used to it.
Engine swap, frame up rebuild (new used frame and body) and transmission swap later, I still drive that darn thing. 300 000 miles and ticking, I can never let it go.
Wife's Grand Cherokee is 210 000 miles, took our family to Yellowstone in 2007 and to Tombstone, AZ and Grand Canyon in 2013 - that will be hard one to let go too.
I feel your pain, Greg, it's like death in the family.