After reading the above (came in late), here are my thoughts:
1. Jib luff length: Find out what the fuller manufacturer has to say about the angle the jib halyard has to make between the swivel and the mast sheave. In the case of the OEM Hood furler, they have a specific angle range.
2. Jib clew height: When the jib is furled it would be a good idea to have it not higher than you can reach, and the height will be a few feet higher than when the jib is deployed. See Stu’s diagram in post #10. The height of the brown(ish) LP line where it meets the fuller should (hopefully) be reachable by standing on the deck.
3. Pulpit: Personal opinion here: I don’t think it matters much if the jib shape is altered a bit by the pulpit because when sailing close hauled and sheeted in tight any shape change is minimal and when way off the wind it will be forward of the pulpit. For the in-between angles I don’t think it’s a big deal ‘cuz like you say, you aren’t racing. If chafe is a concern (no problem on our boat), put some UV material in that area. [Edit: just read Rick's post above on this subject]
4. Sail cloth weight: For the cloth the sail maker will use, the weight will be determined by the sail dimension. In my case I went with the next heavier cloth weight to hopefully increase longevity. The good news: It really worked! After 20 years with thousands of miles under the keel in all kinds of weather the sail shape is, what can I say, marvelous. Really, really good. Have sail-shape pictures from when the sails were new and they’re still excellent. I do take the sails off at the end of the season to prevent mold (that’s what we get around here, right?) but, still, the shape is great.
5. Tall fractional rig: One reef in the main and you gotta masthead rig.
6. Loose foot: The sailmaker asked if I wanted it but I was hit broadsided so kept the bolt rope setup. In hindsight the loose foot would make it easier to take the sail off and put it on again. However, as was mentioned by Stu again (this guy has a lot of good comments), make sure the outhaul is nice and smooth. My boom has a block inside to provide mechanical advantage and it’s a tad harder to pull the outhaul out but helpful if one want’s to winch the clew in tighter.
7. Flatening reef: Make sure the spreader patches cover the area between the non-flattening and flattening reef areas. Heck, maybe even with the first reef in, too, but I don’t reef much off the wind. 40 knots down the Strait of Juan de Fuca, wa-hoo! with a full main!!! Riding the flood from Barkley Sound to Sooke Inlet, could have gone all the way to Port Townsend but had to take a break.
8. Full battens: Wouldn’t go with a full bottom batten again. Not worth the hassle.
9. Jib: Back to this sail again; wouldn’t go too high off the deck with the tack, currently it’s only about six to eight inches, and clew height, wouldn’t go with a Yankee cut again either. Maybe two or three feet but not more. Can’t say that the Yankee cut has ever helped with visibility to justify it. Since the furler is below deck make sure the tack pendant won’t interfere with the steel plate of the anchor roller setup.
9. Mast bend: Make sure the sail cut takes into account the mast bend of the rig and also discuss the fuller sag dimension. Weather helm was discussed earlier and aside from sail shape and dimensions, how the rig is tuned, like mast rake, affects the helm.
10. Main sail: Level boom or raise the clew? If I had to do it over again I’d raise the clew a bit to give more headroom. There’s a good reason why the boom is called the boom! Also, could give a bit more clearance for the dodger (this is the Northwest - we don’t use biminis).
11. Jib UV strip: This is not an option. The typical UV material tends to shrink over time and will cause a hook in the leach, not nice for the picky sail trimmer (c’est moi!). North sewed mine on flat and last year it was removed and new UV put on. HOWEVER!; they used a sticky-back material without mentioning it to me. Asked them what happens when it’s time to replace it and was told to buy a new sail. Between you and me, and everyone else here, that jib is still in really good shape (and they agreed). If that happens I’ll be looking at a different sailmaker.
12. Draft stripes: Nice to have. They can put them on or you can do it yourself. Take pictures when the sail is new.
13. Leach adjustments: Find out what will be used to determine if you like the setup.
That’s all I can think of at the moment, but: “The devil is in the details.” (and there are lots of 'em)
