Read earlier that you'll probably order this winter for the better pricing, so, if that hasn't changed, here are a few thoughts:
Maybe not the original sail? If the boom is drooping, while it may be due to stretching of the sail cloth, it may also be due to the sail not being the original sail. It is possible that the previous owner bought a used sail and it almost fits. There may be some tell-tail signs such as the sail bag markings (although the original sail bag could be reused), spreader wear points on the sail (if it came from a different rig, a sailmaker could probably spot any wear because they know what to look for). It was mentioned earlier that the bolt rope shrinks so if that seems loose and the head of the sail is all the way up, that could be an indication, especially if combined with spreader wear points.
Heavier sail cloth: For the new sail, the sailmaker will come up with a cloth weight based on the sail measurements. However; if the recommended cloth weight is anywhere near the breakpoint for the next heaver cloth, consider getting the heavier one because it'll not get blown out so readily. The incremental cost for the heavier cloth is not a whole lot more.
Draft stripe: Recommend they add one because with a picture looking up the sail the sailmaker can put it on his computer and tell if the shape is good or not. If considering a recut at all, it would be handy on the current sail, and jib. If the sail draft isn't too bad, maybe just have a flattening reef put in and that would take up the slack on the foot of the sail. To raise the boom end, just a single reef point at the clew end however high it's needed and that would be far and away the cheapest way to go, maybe not even need to get a new sail if everything else is okay.
Topping lift: In light wind the topping lift can be used to loosen up the leach to improve sail trim. Without it, the leach can be drawn straight and not provide a good shape. Handy if there isn't a solid vang.