One problem I've had when I got started, and seen keep others from hand sharpening, is their grinding wheels are not round. Bouncing the bit around is not conducive to getting a good grind.
Simply buying a diamond dresser (flat, not point) and getting it flat and round is the first step towards a good drill bit.
Oddly enough, I learned how to hand sharpen drill bits from getting a Drill Doctor 500. Broken bits needed to be close to normal geometry before the DD500 would sharpen them, and I found I could get them really close by hand. What I haven't learned to do by hand is do a split point, something the DD does well.
It's amazing how much grief us DD owners get from some old-school types. On another forum, one guy posted a very long diatribe about getting a negative relief angle and how the DD was useless and would never replace hand sharpening. Too bad he didn't read the extended instructions on how to deal with tight twist drill bits.
And oh yeah, they're not cumbersome and tiresome to use, or cost a ton of money. For one thing I don't need a rule or protractor.
I got mine on closeout when the X models came out, and it's more than paid for itself. I'm a special case, though, I inherited several hundred drill bits, many dull, but all good old US made bits.