For the rolling issue, I add something like this to my Wacom pens that roll:
Then I can hook it to the aforementioned “pen loop” that I affix to my case.
Some other things I like about the Wacom, I often replace the plastic nib with one made of hard felt and it gives me that “draggy” paper feel. Second, I like the variety of pens available, everything from heavy weighted, to fountain pen, to BIC like pens, to tiny ones that fit in phones.
I have almost a dozen of them. Most tablet PCs for the past ten years have used the same pen technology. So, if I search hard enough, I can find a “discard” on Ebay for a few dollars. Finally, I like how you don’t have to charge it or don’t need an AAAA battery (although you pay for it with more device battery usage required to power the digitizer)
One thing I don’t like is, depending on the pen and device, you might get an offset between tip and display that is large enough to be annoying.
From what I’ve been told, the Pencil is pretty good, and it will be interesting to see what the next iteration brings. Hopefully that will force Wacom to step up their game.