I have not studied Kempo but I will add my understanding of what High Level Skill is according to the art I practise.
When you first start out at any art, there are the fundamentals, set techniques, correct posture, basic concepts, awareness etc. The more you practise each technique the more you can understand the underpinning concept behind it, why does this work? When you can understand a concept it gives the student a wider choice of how to fight, allowing them to not think of techniques they learnt in class, but instead be more dynamic and flow from one technique to another according to the situation. Beyond this is understanding the timing of a fight, to be able to gauge distances, anticipate primary, secondary and tertiary strikes and allow your opponent to throw them. Once you can anticipate, you will be able to make your opponent move and stirke in the way YOU want him to, by controlling the fight, angles, distances, tempo, you can choose which openings you offer the opponent without making them look like blatent baits. Higher then that would be to syncronise yourself with your opponent perfectly and then ruin his timing, as what he expected has now totally been changed. Once all this has been attained, you should be able to amalgamate it all together so that you use your skill to the level it is required when it is required, "gears" to put it into words. Your ability should become instinctive and should happen by itself without even thinking, due to your experience and ability to calculate high levels of combinations, scenarios, counters and counter-counters.
But to get to that stage, requires enormous amounts of practise and honing of skill. I personally dont feel there is a cieling of skill, as skill has no limit, you could take a whole lifetime of training and just keep getting sharper and sharper.
