If you order sails from one of the main builders, Jotz, North, Cressy/Doyle, I believe they will be cut generaly for the tapered masts. So I dont think any accomodation for a straight mast without the jumper stays, would be necessary. When I bought my first set of sails from Jotz (1992) I mentioned that I had the untapered Alspar mast. He said his sails worked on either mast with the same cut. My racing seemed to prove that out. 1994 PCC 1st. Then I replaced the bent Alspar, 1996, I continued to use that same original set of sails for 4 more years on a taperer mast, and won 2 NACR and 1 PCC with them. (Please forgive the boast, I only want to make the point that the sails work well on both kinds of mast) I used that same set of sails in a local regatta last weekend. I only use my best set of sails for top regattas, and that way I keep them competitive for about 5 -7 years.
The Jibs I use do have a small diameter rope in the luff instead wire. Originally it was because that was how the jibs came from the builder. After using that simple system where the Jib Halyard is used for the cloth tension and the forestay tensions the rig and jib sag, I found that it worked well enough that changing to an adjustable jib luff wire and adding a jib cunningham didnt make sense for my boat. To make this jib system work, a 3 or 4 to 1 purchase is needed for the jib halyard to get enough luff tension. Most of the rigging systems on my boat were the simplest I could come up with, and I would then see what the 'Big boys" where doing and I would copy them. Over the years, very little has been changed. Just a minor tweek here and there.
Lollipops make the crew (my kids) happier. you know what they say about a happy crew. However........ handing them out on the water has cost me one mast, and numerous dings, including a big side scrape from a Laser last weekend. As far as reading wind shifts, I leave that to me crew, I am always busy trying to keep those darn yarns flying on the jib luff.
phill
ps. I have no affiliation or deals with any sailmakers.