I use a Climax setup also. Dad origionally bought it some 20 years ago. At some point in time he came up with a mike that will set on the bar and measure the protrusion of the bit. I can find out from him exactly what it was origionally designed for but it only works with the 1/4 shank bits, not the 3/8. That said at one point I think Clima made a tool specifically to use with their bars that did the same thing. Beyond that, when the mike won't work for whatever reason, I simply us the depth part of a standard caliper, set square against the shank of the bit, to get my measurement.
For larger bores we've made quite a few split collers that clamp to the bar and hold the bit. With them I simply take a cut and measure it for my hole diameter, without regard to the protrusion of the bit, until I get close to the final bore diameter. At that point I leave the bit alone and simply loosen the collar and ad shims of half the amount I want to take out of the hole under the side of the collar holding the bit. It works like a charm and eliminates any creep from the bit, etc that would screw up the final diameter of the hole, so it makes getting the hole accutately sized much easier than setting the bit height off the bar alone.
Something else I do when boring a hole is I use one of the chisel cut Sharpies to mark my bits. Once I get the initial protrusion and make a cut I mark the side of the bit where it meets the bar. With that mark in place I loosen the set screw and push the bit out until the mark is somewhere around the height off the bar of the cut amount I want to take.
Dad started boring back in the 80's and taught me all of these tricks, and I've been using them all myself for close to 14 years and they all work great and make the job alot easier.