I don't think it's any sort of all-or-nothing one approach or the other. For any given item of gear, decide which 'version' is best based on multiple factors, with weight (for me at least) being quite an important one. It also depends, for me, on where I'm going and at what pace.
So of the specific issues addressed:
"However, the new tent isn't freestanding and can't be pitched fly-first (a factor in Ohio rain), and I'm still not fully convinced of the durability of the pole; the water filter is much harder to clean in the field, and somehow seems more delicate; the NeoAir is more delicate and more of a pain to inflate than the old Prolite, and so forth. With the "old" set of gear, everything worked so well and so simply that gear sort of faded into the background, and didn't take much thought or time to deal with; none of it had ever failed. The "new" stuff has never failed either, so durability and function aren't issues. It comes down more to attention and convenience. The new stuff seems to have me spending a lot of time fussing with gear: instead of filtering directly from the stream, I now fill a nylon bowl and filter from that to minimize filter clogging; I spend a lot of effort blowing up the pad, and am reluctant to use it for anything but sleeping; and I'm a lot more worried about where I put the tent. I notice that the lighter pack, even with less weight in it, doesn't do as good a job of keeping the weight off my shoulders; I also have to cinch the more lightly-padded belt tighter to transfer the load. I find I notice the pack more when I'm walking, and do more fiddling with the straps and such, and that I frequently reach lunch or camp with tired (but not sore) shoulders and hips."
Tent issues: I personally don't see the problem with tent pitch. For me, at least, it doesn't take so long to set up my not-freestanding tent that I would consider that as a factor. ? It rains a lot where I live too.
Durability of the pole: can't comment there, not enough data. Well, but one thing to consider is how easy or hard it might be to field repair if it broke. My own tent uses a little plastic ridge pole that is essential, and it's not a super strong thing. I can easily imagine it breaking. But I wrap it up carefully in the tent each time, and when it's not so-protected, it's in place in the tent under static (not dynamic) loading. So I'm comfortable with it.
Water filter harder to clean: consider using aqua mira drops, plus something to pre-filter if that's an issue for you (I have hardly ever had to do this). Not too expensive to try this out.
NeoAir: more of a pain to inflate for me is offset by "thicker, more comfortable, particularly on rough terrain". More delicate: bring a patch kit. I've used a first gen. neoair on two thru-hikes now and still use both of them; one is slightly delaminated at the head end and has one patch on it, but ... so what? They're not that delicate if you take care.
Pack putting too much weight on shoulders. I'm with you, if you can't fix that then I think you don't have the right pack. Though going the *other* direction (lightening up further) can mitigate that if it's not currently a big problem.
Consider this year doing one trip with your "new" gear, and then shortly follow it with a trip with nothing but your "old" gear. See how happy you are offsetting weight savings with mental and physical comforts.
For my own part, if I'm having issues with a piece of light gear, I don't think in terms of going back. I'm willing if it's the right answer, but generally the right answer for me is to figure out and solve the issue at hand.
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