Should I watch Shippuden after "Rewatching" Naruto?
I put it in quotes because I never really watched more than a handful of episodes when it was on toonami as a kid, this was also around the time when there was the big rivalry between the big 3 and I was more a bleach fan. Watching all with a bit of foreknowledge I'm surprised to like it a lot more than I would've initially thought. I've got my complaints sure but that was to be expected.
The problem is I know the direction it's going in after this and I've talked to a friend about this, what I really liked was the tactics and use of ninja tools but then after the timeskip it turns into a "my jutsu is bigger than your jutsu". I'm exaggerating here, but that's how I've heard it basically turns out, with that only Naruto and Saskue have any relevance as they are both ninja Jesus? Again I've never watched Shippuden all my knowledge is secondhand, mostly memes and video essays.
Should I continue into Shippuden or should I save myself the disappointment? Because I know that the things I liked in the first half won't be expanded upon and the direction the story seems to go down a very different direction from the hard work vs talent story (which doesn't sit right with me when only 3 of the konha 12 don't have a clan) to "breaking the cycle of hate"?
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Shippuden is really good and pretty much well written BUT there is a lot of filler and you can skip a lot of it but some are definitely needed to be watched
What you're describing is basically the Fourth Great Ninja War which is the last arc of the series (400 eps or so).
Akatsuki fights were still pretty tactical especially the earlier arcs in Shippuden. I won't say which fights but there were Akatsuki fights where Ninja Tools were an integral part of the battle.
Shippuden suffers from One Piece Pace a LOT in some arcs, look up what episodes are filler because there are a LOT, like I'm talking straight up a year went by once and we only had 3-4 canon episodes that year.
But if the pacing of canon doesn't kill your interest go with it until the 260ish episode then switch to the manga and watch the anime for the cool fights and hype/sad moments until the final FINAL(you'll know when you see it) part then you should watch the anime from there until the end
AND THEN
Watch Naruto: The Last Movie & Boruto: The Movie, nothing else of Boruto, the movie is worth watching as a nice sort of round out of the series
Also skip the fillers, DEFINITELY skip the fillers
For me, OG Naruto is a 7.5 meanwhile Shippuden is a 9
And out of all the fantasy fighting animes naruto is the least my jutsu is bigger than your jutsu
I'm aware of how bad the power creep will get, and I'm definitely not looking forward to that, but it'll be worth a few laughs, at least