My 99 jeep cherokee 4x4 is one of the most reliable vehicles I have ever seen.
It has 193,xxx miles on it.
Have had not rebuilt motor or tranny.
Just regular maintenance and what not. And I have lifted it and new wheels and tires and a paint job!
Total less than 6k Into my jeep in the past almost 5 years I have owned it. Maybe closer to 4 years.
I replaced the oil filter adapter O-rings yesterday actually! Those will be good for another 193,xxx miles!!
It gets driven more than my pony prolly! Just cuz I refuse to drive it to school.... I have had to many doors smack my jeep and one kid side swiped it while was pulling out.
I do not want anybody F'ing up my pony. So I use my jeep as work/school vehicle. And off road vehicle!
And drive my mustang everywhere else mainly college classes and Alabama
and to visit my girlfriend and dates and what not.
Point being, you can have a nice dependable older vehicle, it's all in how you take care of it and how it's been taken care of.
If I had your classic I would not trade it for a newer any day of the week if I had the option not too!
The allure of that 5.0 would be hard to resist... But I guarantee you have a much more unique vehicle right now than you ever will with the newer 5.0.
Just my thoughts...