To address at least one of your three questions . . .
"3. With these new chucks (Roc and Carve Tight) what is the best way for indexing the bits when doing a project? In other words, if you need to replace a bit during a carving, and you did the usual setup on starting the project, how do you get the bit shakes slipped back into the chuck at the same depth you used during setup?"
I entered the game with a B model CW and the Quick Chuck. Changed that for a Roc chuck early on and loving it to this day. Since I have quite a few 1/2" shank bits I looked at all sorts of methods to index them to the same length when inserted. Going for the simple method, I wrap 2 or 3 turns of 1/4" wide masking tape around the shaft of the bit. When it contacts the bottom of the chuck jaws I can feel that I've inserted it far enough and I tighten the chuck. The low cost KISS principle works again.