What you are seeing is normal in hollow tip (covered point, as Country says; a.k.a. non-expanding hollow point, as the military calls it) match bullets. Its due to the point being drawn after the cup is trimmed, and the trimming not flowing perfectly symmetrically in the final steps. You'll see some of these tips are square and some are slightly angled, which is what causes the issue. it doesn't significantly affect flight, but it's there.
The Hornady aluminum comparator inserts for ogive measuring will hit the bullet closest to where a seater die does. The stainless ones sold by Sinclair will hit them closer to where the actual throat does, as they are wider and contact the ogive further down. There are times I use both.
I prefer the Redding Competition Bullet seater dies, despite their cost. They make a special seater stem for VLD's if you are shooting those. I've seen a couple of tests where they've beat all others, possibly due to their floating seater stem. The main thing, though is consistency. Dave Milosovich ran the Wilson, RCBS Competition seater, and an RCBS standard seater for comparison in the Precision Shooting Reloading Guide. The standard RCBS, which has a long, thin stem rod that flexes enough to approximate a floating seating ram, actually did best for him. The RCBS match seater didn't do as well, something I've seen replicated elsewhere. The Wilson did worst in that instance. Here's another test, but one in which the Wilson outperforms the standard RCBS die
done by German Salazer. But the Redding beat both in that test.
If you can't get the Berger's to shoot and it seems to defy explanation, read this from Berger