Originally Posted by MedSailor
Is there any reason that I shouldn't just have the sail built so that the boom stays level with each reef?
Probably not, unless you do intend to reach/run in big seas when reefed. If you're hanging around the San Juans primarily, or inside waters of BC you may not need the 'clearance' that the high clew provides.
Certainly if you're getting a new sail made you should have it made how you want it. If you're close to buying a sail, have your sailmaker look at what you've got (on the boat so he can see the setup) no doubt he'd have some input.