I guess admit that I have a warped view of the world, but . . . I look at the first and second generations as two different trucks.
First gen, 1983 to 1988, is the last of the "old".
Flat nosed as a brick; glass headlights (which IMHO perform better than the later plastic lights); a bumper that looks like an afterthought; archaic interior (as in "truck") with a lot more exposed metal and steam-driven controls; 3-hole radios (which God himself invented; in the '83-'84s); carburetor motors (with some). If you learned to drive, or drove, '50s, 60s and 70s iron, the first gen is like an old friend that you haven't seen in ages.
Second gen, 1989 to 1992, is the first of the "new".
Rounded "aero" nose, plastic headlights with plug-in bulbs (yes, much more convenient); the bumper is part of the of body lines; much more plush and comfortable interior (as in "car") and no exposed interior metal (in upper trims); DIN radios, better speakers and better controls; fuel injection and even better engine management (granted, it's still OBD1). Availability of the 4.0L six (and, the 2.3L was an excellent motor by these years). The second generation is much more refined, and more comfortable to boot.
My best and most trusted sensory unit, my "buttmeter", thinks that driving the first gen is more like driving the classic '60s iron, and driving the second gen is more like driving a funky, retro version of the same crap that you buy new these days, but without all the tech nannies, the high-tech BS that a transporter doesn't need, and the built-in enslavement to the dealership.
Honestly, at this point in the game, you can't go wrong with either generation.
You're getting excellent advice so far; the only thing that I can add, is to be patient, and get the truck that really "speaks" to you.