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Fuel injection! Overdrive tranny! Seem to be more trucks with the luxuries like AC, intermittent wipers, electric door locks and windows and cruise control.
Newer trucks have more amenities, and more crap on them (efi, computers, smog, etc). Older trucks have less of both, and tend to be bare-bones mechanically, so they're somewhat easier to work on. Parts availability for older trucks may present a problem in your locale, but you can always use the internet for small stuff. Mostly, it comes down to what you want or what you like best. I love square headlights and brutish stances for trucks; so it's 78-86 F-250 and up 4x4s for me. Plus that's what I grew up with. My buddy likes any stepside 4x4, regardless of year. Pick what you like and make it into what you want. That's the fun of owning and building trucks. Otherwise, it's a lot like work. My $.02
Thats a hard choice, both styles are great in their own ways, I bought my 86 F-250 cause it had a 460 and a 4spd, I love big blocks, the earlier trucks are far simpler, they didn't have to meet such strict emissions so you won't find air pumps and catalitic converters and EGR type stuff, one thing you'll find with the new truck is you'll need two sets of tools, my truck has metric all over the place !
And the '67-'72 bumpside trucks look the best of all.
I had a fun '72 F-250 with a hot rodded 390-FE.
I like my new '85 better.
It's not quite as good looking, but it sure is more reliable (and I haven't had to call the tow truck yet).
I'm still hoping someone will make a phantom full-size Bronco out of a 67-72 bumpside truck. Now, **that** would be sweet!