I'm all outta gear man!

Ok the trick to 'flying' a sail, easily, before you waterstart is:
1. Lift it out of the water
at the top of the mast/mast tip. Always. It's easy-peasy up there.
2. Try to make sure the mast side of the sail is on the windward/windy side, ie it's pointing the right way.
If not it is often easier to swim it around to the other side of the board, get if flying (see #1), and flip it before you water start.
Sometimes it is possible to get it flying the wrong way and it'll flip all of a sudden for you. Easy to handle when you're at the top of the mast, eh?
Once you get the top of the sail out of the water the rest often pulls itself out too.
3. Waterstart slowly and carefully, else you'll be back in the water all over again. Stitch in time... yada yada.
Exceptions: If the rig ends up with the mast pointing straight down... too bad. You're gonna get a little tired. Getting fit can be a side effect of windsurfing.
Just remember rule #1, and the rest will fall into place anyway.