Re: new sails
The price differences come down to where the sail is plotted, where it is sewn, and what materials are used. The material choice isn't only in the sail cloth (what is normally talked about), but also the type of battens (tapered or not), how the batten pockets are sewn and tensioned, how the sail slugs are attached to the sail, how many reefs you have, etc. I've found it pretty easy to see these differences when looking at a few different sails.
I have a friend who recently owned a Catalina 22 and in the last year he bought a new Rolly Tasker jib and North Direct main. He felt like the main was a better made sail with better attention to the details, but both were major improvements over what he had before. I didn't look closely enough at each sail myself to have strong feedback either way.
If you stated where you are located then someone may be able to recommend a local loft. I got competitive pricing and a really great sail for my Catalina 25 by working with an independent local loft.
boats that I sail on regularly: Pearson 28-2, Rondar 505, Yankee 30, Blanchard Junior