I skip, pitch skip, and backhand skip with a baitcaster. If you have a bait that skips well, its all about your rod tip and your release point. I skip with a 7MH TFO Signature Series. This rod has a super soft tip, almost feels like a crankbait rod.
The lighter the weight of the better, but with a baitcaster, you're probably gonna want to not go lower than 1/4 oz. I pretty much just skip arky head jigs and paddle tails. The trailer does matter on your jig. Chunk trailers with long flappy claws don't skip as well as twin tail trailers or beavers. I usually have a 1/2 oz arky jig with a beaver trailer tied on. I wouldn't try to learn with 1/2 oz though. 1/4-3/8 are good starting points. The head design matters as well. Arkies skip the best. Footballs skip all right. Swim jig heads and brush heads take some practice. Paddletails skip really well, but it tends to wear them out a lot quicker. The screw that goes in there nose tears out while skipping. I always use a 3/16 oz keel weighted hook for paddle tails.
As far as the technique, its just a roll cast with a lower delivery, it's all in the wrist. I keep my settings loose. On a Curado I, I have the mechanical break almost turned off, two brakes in use, and set to 3-4 or the dial. I use the same setting for casting.
Big flat braided line would help you skip better than 8 lb fluoro. I skip with round braid like smackdown or fx2 and a fluoro leader.
Once you get your release point down, it's no big deal. I skip even when I don't need to sometimes just because it's a softer presentation. I almost always skip to laydowns just because it looks more natural and when you skip to a laydown, it gets you as close as possible to the cover.