Lots of good info in your post.
Jet it to run well. If the smaller pilot helped and the bike isn't showing signs of being lean it sounds like the right move. I wouldn't worry about it being 'too lean'. It'll show signs like not settling back to idle or falling flat and hesitating at small openings. That needle has a very short straight section which transitions onto the taper quite early compared to others too.
PV sounds good.
Head o-rings could be re-used, as can most o-rings. But.. if they leak afterwards you'll end up losing coolant either internally or externally. Cheap insurance? I'd probably aim at 50-60hrs to do top end insp and squish.
Qstealth is a spoogemaster for sure. I have 2 x 250s both set up very similarly. One uses a TCII with no spooge, the other Qstealth and drips. Same fuels and oils in the same area.
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