I'm not a fan of using wear comp for cutter comp, but if I were , I would tend to bias the original tool diameter description so that the compensated path (with some wear amount) is always larger than the programmed path. As you may know, offsetting a profile outwards creates a legal path, but offsetting inwards may lead to cutter interference issues when certain radii and/or intersections disappear from the path.
First you get good, then you get fast. Then grouchiness sets in.
(Note: The opinions expressed in this post are my own and are not necessarily those of CNCzone and its management)