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It does mean some things. You won't find a hundred episode anime with great animation quality. There'd have to be an insane budget to give some of the perks that shorter anime have to longer ones.
Most short series don't have particularly high animation quality though. Longer shounen titles just use their budget during the moments that matter.....actually that is a lie, if you're Shippuden staff you use your best animation and art direction in filler arcs.
I can't complain, Naruto vs. Sasuke was my favorite part of Naruto/Shippuden. But shorter anime can still manage higher quality, usually, simply for financial reasons.
He usually is, must his sensibility must've been clouded from just having finished the show.
Doing anything just after finishing a good anime is usually a bad idea.