What's odd...Is I can't skip anything but a frog!?

I can get that badboy into tight spots. I do trim my legs (skirt) and use the smaller frogs as well. Spro frogs are my go to for this.

I'd say Mop jigs are the easiest to skip. Get a 3/8 oz buckeye mop and go to town.

I have some trouble sometimes skipping a Spro type hollow body frog but can skip a Ribbit with no problem.

I prefer to skip a swim jig either the 6th sense divine or strike king, use a flat trailer like a z-craw. I would then graduate to a senko and then a frog. Another tip is to take some of the line off of your reel as you won't be casting it as far. My go to rod for skipping is a Falcon lowrider lizard dragger. It still has a backbone and nice tip.

Try skipping a toad.

Skipping is a product of the rod.... stiff rods are terrible for learning and have a very large learning curve. I skip better going down a rod size for the bait. For jigs drop to MH action, I skip a fluke and senko on medium action, though I hate fishing senko on medium. You need the rod flex to fire the bait quick and you need to learn how to tap your spool without stopping it. Fire the bait parallel to the water and try and get the first skip in the 1st 15 yards. I do a 2 tap skip. I tap the spool on water contact but don't stop it, then I thumb it. My thumb doesn't really come off the spool ever. Adding pressure is more like tapping the spool. Practice with a senko, it really bounces. Also pay attention to your rod position, raising your rod tip up towards the end allows you to help aim the skip, and pull a few feet of over run out. For frogs, shorten the legs. Chatterbaits skip very good. Long worms are horrible for skipping, but I can get a 10 inch pretty far under a walkway. Expect some backlash, but at some point you should be able to make it manageable