Hello Brian.. A couple of years ago, I had the opportunity to style a large, old tsukumo cypress for the owner of the nursery that I go to. This tree can have extremely bad die back if not taken care of and pruned properly. Also, if you do cut the foliage, you should only cut back or pinch to where is is still light green. Trimming beyond the green or to old, dark green foliage may yield that area incapable of producing new foliage.
I think that this tree is in good shape. I would just designate the main, side, back, and a couple of front branches and then wire accordingly. If there is already some dieback in the interior, you may have to put alot of movement in the branches. This will shorten the branches so that the foliage appears closer to the trunk. Also, you may want to leave more branches than you need... just in case a branch dies. Also, in my opinion, I would not style cypress in Fall, but wait until Winter is completely over. This is because if you style in the Fall and then branches begin to die during the winter, you could be left with quite a bare looking tree. In Spring, you will know what is alive and what can be worked with.
I hope this is helpful
