BJ,
Winchester produced brass for large pistol non-toxic primers for a time. Those all had flash holes about ⅛ inch in diameter. This was because the DDNT sensitizer used in non-toxic primers has higher brisance than the lead styphnate used in conventional primers. As a result, if you used a DDNT primer with a standard size flash hole, it would make gas so fast that it would blow the primer back hard enough to cause subsequent piercing when the chamber pressure peaked. Usually, you see the initial NT for non-toxic stamped on these cases. People I know have reloaded them with conventional primers and reported no problem, but that is anecdotal and I would either scrap them or set them aside for use with primer-fired wax or plastic bullets, as those require the same larger flash hole.
Lack of friction in the sizing die is an indication your brass is being fired at low enough pressure not to expand completely into the chamber and I've found it tends to happen because a case has a fairly thin wall where it grasps the bullet and has work-hardened to a level of springiness that assists to prevent full expansion into the chamber. R-P (Remington) brass is particularly noted for this, having only a 0.010" thick neck wall. I used to toss it because, though I could still feel it touch the sides of my Lyman carbide die, it would not resize enough to hang onto a bullet well. I could push lubricated lead bullets into these cases with my thumb, and occasionally I would have a bullet actually fall into the case mouth with no hold at all. Later, when I got a Dillon press, the problem stopped. it turns out the Dillon sizing dies are on the snug size and they would get the R-P cases squeezed down enough to hold onto a bullet, regardless of what they did in the chamber.
Regarding flash holes, I've seen a lot of those way-off-center holes in Fiocchi brass, too. It looks like they are drilling them without a bushing that centers the drill in the primer pocket or else they have the drill bit extend too far beyond the bushing so it can walk. However, the fact these are off-center does not mean they won't work. If off-center flash holes couldn't work, Berdan priming wouldn't work. It's more a matter of how consistent the flash is. And while that can become significant to ignition consistency in long-range rifle shooting, I am not aware of it mattering to handgun ammunition fired at 50 yards and under.