Ok, get ready to laugh.
Get you a stout rod with fast tip, use Zebco 33 with 10 lb. line
NO MORE BACK LASHES, YES, IT WORKS.
May have to give up your Man card though! Enjoy

Start low.... End low...

I skip lures from time to time, sometimes well, and then not too well, both with casting and spinning. There was one deal that surprised me though. I have a 6.5 ft spinning rod and got a 7ft 2in for more casting distance not skipping. But I found that the 7 ft 2 in skips like a beech, way better for me than the 6.5. At least for me, the rod length and action made a huge difference.

Speed and angle help a lot. Think of how you skip a rock.

It is all about the setup. I use a medium heavy 7' rod and a Citica reel. Make sure your break is set up correctly. I know my break is adjusted right when I reel the bait just past the half way point on the rod. I then hit the button on the reel and let the bait fall into my hand. When the bait stops the spool on the reel should stop too with no backlash occuring. This is very important. If you get backlash then tighten your break just a little. Reel up and try again until you find the correct adjustment. When you find this your half way to skipping.

I suggest yzou start with a 1/4 oz jig. Use your thumb to feather the spool as you cast. Someone said think about skipping a rock. That is exactly what I think about. A fast tip on your rod is very important. Practice and more practice is all I can tell you but with your reel adjusted correctly you will figured it out fast.

Oh yeah, braid works best for skipping. I use 40 lb braid.

Anyone using 10lb line under a dock is asking for it. . .

You ever seen the stuff in the water under peoples docks? Not to mention the dock itself. One single pull around a dock pole can break 10lb line. If you have on some 17lb Big Game, that isn't near as much an issue.

I have to disagree with that, when I am skipping I want the spool very loose, yes a back lash is more likely but once you get used to it you will be able to skip twice as far. Just use your thumb to control it.

The best advice I can give you is to back off your cast control brake (loosen it) and turn up your magnetic or centrifical brake. Keep your cast angle low and concentrate on keping your bait as close to the water as possible as soon as you start the forward motion of your cast.

Practice makes perfect...Good luck!

Just like skipping a rock, it's all about the angle in which the bait hits the water. You create the angle by sidearm or roll casting. I believe the speed of the cast is very important. Without speed the lure will not accelerate when it hits the water.

Here are a couple videos on skipping:
http://www.youtube.com/watch?v=2tXlODzLu4A
http://www.youtube.com/watch?v=KYzCqmkU24g
James Biggs has one as well.

I don't see why this wouldn't work.

no expert at all, but I first started skipping lures across open water while fishing a point. Takes the dock out of the equation, and you can watch how the lure skips across the water.

Your gear is mostly personal preference. I've seen people skip like champs with everything from light spinning tackle to heavy flipping gear. Generally speaking, braid is a bit more forgiving if you are just learning. You can debate set up and line size for hours but having spent considerable time skipping over the last several years I can tell you two things. First, many people get WAY TOO CLOSE to try to skip under whatever the structure they are fishing. Docks, overhangs, cables, whatever. If possible get back a little farther and try again. You'll be surprised how much this helps. Second, getting your bait on plane as quickly as possible greatly increases your success rate here. The sharper the angle you hit the water at, the more likely you are to backlash or not get your bait where you were aiming. Both points are related because backing up usually improves your approach angle. As you get better, move in and work on more on roll casting or backhanding. Starting with these techniques doubles the length of your learning curve�.
Good luck.

Just out of curiosity, I'm wondering what it would be worth to a serious tournament angler or full-time pro to be able to consistently and accurately skip a weightless or t-rigged plastic bait 25-40 feet under a dock or overhanging tree? Any bidders?

Most of them already can!