Okay I have a couple questions here. First, how do you peg your weights, and why? Second, how do you skip your baits, when, and why? And third, How do you rig weightless? When should you use it, how, and why?

Pegging: I just get a normal rubber band, snap it in half, and tie an overhand knot with it right above my weight. I only peg my weight when I'm fishing heavy cover (to reduce hangups) or when I'm fishing very clear water (to provide a more realistic, compact presentation)

Skipping: skipping is pretty easy with spinning gear, but it can get kinda tough with casting gear. Rig up a weightless senko or trickworm on a 6'6"-6' M or MH spinning rod, then approach a target such as a dock, now lower your rod tip and make a quick sidearm snap cast. The bait skip effortlessly under the dock, and with time and practice you will get increased distance and accuracy. Now with casting gear you need a heavier bait like a 3/8 or 5/16oz jig, rig that up and approach the dock, then make a very quick and powerful pitch that is very low to the water, the jig should splat several times right on the bottom of the jighead. The key to skipping with casting gear is to train your thumb to feather the spool at the right times throughout the cast, if you don't then you will wind up with a backlash of biblical proportions.  

Weightless: A weightless rig is a texas rig without the weight. Take a senko, trickworm, or fluke and rig it weedless with no weight, I use this rig when fish are very shallow and they want a bait with a slow fall.

Pegging: never felt a need for it, if I want my weight to stay near the bait I'll throw a jig

Skipping: wish I knew how

Weightless: when I need a slow rate of fall, T-Rig, Wacky ect

pegging: I break the end of a toothpick off  so it is just a little smaller than my bullet sinker. Then I shove the toothpick into the back side of the sinker. Then, I slide the sinker down until it is snug with the bait. If you can't move it, you might have too big of a piece.

skipping: Use a spinning rod for skipping. I skip mostly un-weighted plastic lures. It works great for unders docks or fish that are chasing shad on top. I keep my rod tip low to the water and make a fast side are jerk. Practice helps A LOT.

Weightless: I use weigtless when the fish are shallow or when I'm fishing heavy weeds, lily pads, or other structure that I want to fish over.