I like the idea of having the gaff 'peaked up' more than is often the case with gaff mains. How many of us are going to go to the trouble of rigging a topsail to fill that gap when we need it?
A gaffer of this size starts to feel the pace as the winds go through the 18 to 20 knot range and my ideal would be a flattening reef that could be put in without the need to let go halyards and lifts. The main purpose would be to really flatten out the main to get rid of the weather helm that arrives around this time.
I would also like to see three more reefing points with the top one higher than is shown here. That ris going to give you more choice to maintain the drive you need in rough conditions and perhaps allow you to carry a bit more headsail than would otherwise be the case.
The top mast need only be high enough for the forstay for the jib. Anything else is just windage and top weight and anyway it will do all in its power to bend forward.
The romance of the cutter is all very nice but I can tell you that often you just want to sail with an efficient rig and the least work to do the better.
First let me say that I believe furlers on both headsails are a godsend and if you plan for them you can keep the cost down a lot. For example if the length of the two foils can be got out of one stock section you have just halved the cost of the foils.
As well on a gaffer with a wooden mast it is difficult to get both foils/stays tensioned up at the same time. I am an advocate of having the drum fastened straight onto the stem and bowsprit fittings and no rigging screws. Instead both stayls/foils are on rope to efsw rope halyards coming down to a gun tackle arrangement on the foot of the mast. You can adjust your forestays to suit, You can slacken them off to stop loading on the mast when parked. AND would you believe you can drop the whole foil and sail on deck out of harms way or for maintenance.
Your bobstay has to be on another tackle off the inner end of the bowsprit so you can further adjust your stay/foil tensions.
I would also like to have the staysail cut so it does not overlap the mast so it can be boomed. It is technically possible to have both a furler and a club foot on the same sail. The sail is cut a lot higher than I am used to. The reason for that is the expectation that you would use this sail as your first choice of headsail in a wide range of conditions. Nice and easy to tack and only one headsail to handle when you are tacking with the jib set.
When on a reach or with the wind aft the boomed staysail can be set most efficiently with very little effort.
So we come to the jib. In my mind I have relegated the sail to being an extra. A very nice extra too if it is on a furler. I am sure with this setup you could do away with it altogether and still sleep nights but I like having it there most of the time.