John,
when windsurfing I assume you let the sail 'slide' forwards a bit just as you startet applying tension to the uphaul? I find it much easier to get the sail ut again with that little slide in the beginning, if it is not windy enough to waterstart.
When righting the T, we let loose downhaul, mainsheet and traveller. This makes it very much easier to get the process started as the main sheds water easier/faster.
