Is your boom height so high that you cannot put the boom arm on the back of the board?
If your boom is off the back of the board, then about the only ption is to grab the back footstrap and rest the boom on your forearm until the wind pick up your sail.
But my guess would be that at your sailing venues, there really isn't enough wind most of the time to get your sail "flying" enough for a waterstart.
So, uphauling is the better option.
Yes, being underpowered and unable to get onto a plane easily would be the primary issue in many of the problems you seem to be having.
What prevents you from sailing powered up to "overpowered"?
Then things like getting into the footstraps, jibing, committing your full weight to the harness, all become easy to do as the sail takes most of your weight and the board doesn't have to support you.
Hope this helps,
Last edited by Roger; 6th June 2008 at 02:24 AM.