the NES controllers were really thin back in the day. The wiimote's fine in that way unless you play for a real long time.

I've never had a problem with it and I bought mine before the Jackets came out. I'd say try it without the Jacket first just to see. I actually find it pretty awesome just to flip the controller on its side and start playing. I've played VC games for many hours in one setting.

The original NES controller's d-pad was pretty soft actually as was the SNES'.

The most painful d-pad had to be the original 3-button Genesis controller.

Anyway, the Wiimote's d-pad is pretty... crappy for extended play.

Playing Chocobo's Dungeon with the Wiimote holding horizontal felt absolutely brilliant.
Far superior to the actual classic controller.
But maybe that's just me... :)
Sonic and the Secret Rings is next on my list.So hopefully horizontal mode works fine there too.

I've tried playing with the jacket and it seems to be a little less painful. Thanks for the tip.

I have the very same issues with the classic controller. It feels too small and I can't even say that I have big hands.

What I wanted in Wario Land is option to use the Gamecube controller. Maybe some of you don't find the Wiimote's d-pad as painful as I do, but I bet that you all prefer the Gamecube controller instead of using the Wiimote horizontal.

I played all of Kirby's Adventure, Legend of Zelda, Ninja Gaiden and some other VC games with the Wiimote turned sideways. As well as Super Paper Mario and Fire Emblem. I just don't find a problem with it. Perhaps you're holding it in a weird way.