Bob,
You have asked some cogent questions.
All our budgets are limited, but if you are willing to "bite the bullet," as you say, then I would suggest that you deal with the name lofts in your area. One thing you need to do is get competitive quotes. All the measurements that will apply to your boat are already in a computer, so the hands-on measuring that used to mean a lot is probably an unnecessary step now.
I would think that if you put a roller up front--ProFurl seems to be the one these days--then you are dealing in personal choice. No one can help you make that decicion. Additionally, you seem to be well informed. On the down side, a roller limits the number of sails you can fly easily. I have jibs in a diverse range...storm, working, 155, 190 and an asymmetrical chute. They all mount in the same place and in the same way, which I consider a real convenience.
In addition, I have my jib sheets eye-spliced into a Tylaska shackle's bail, so when I change jibs I don't have to change sheets. We can tack my boat nearly as fast as an America's Cup boat. Nothing ever hangs up on the forward lowers. Even though I use hanked-on jibs, sail changes (when necessary) are pretty swift.
Personally, I use dacron. That's because it works for me. If it did not, then I suppose that I would move to another cloth. Dacron is nearly indestructible and lasts a long time. It won't give you the sail shape that Mylar, Kevlar and Spectra will, but I think it gives you the most bang for the buck.
To let you know that it isn't ALL about sails, I sail with a 12-year-old main, a three-year-old 155 gennie and a 30-year-old working jib. People who race around here have told the president of my PHRF organization that my boat (1973 E-27) is so fast that it could not POSSIBLY be legal.
About fully battened mains... My own, personal jury is out on that. I raced from Ft. Lauderdale to Key West a few years back on a Palmer-Johnson 77. They had a fully battened main. In light air, the top of the sail wouldn't come across in a tack. I thought it was a real pain. Maybe that was just a problem with that particular sail. I am not certain. But it can exist.
Going with a name loft as opposed as the smaller guys? I'd go with the "name." That's because they have to give you good service, and will. Their reputation demands it. Sometimes, it is the little extras that you get that make the real difference. And, honestly, having a good loft's logo on your sails tell others that you have the taste, experience and, yes, money to go where others without your great sense of discernment fear to go. Remember, sails are your engines. A Ferrari will get you where you want to go faster than a Yugo.
There, you got it all. But it's your money and your choice. Good luck.
Morgan Stinemetz