RE: the whole life jacket thing
Looks pretty good to me!
I'd say your boom needs to be higher, and until the board has totally dropped over it's bow wave (it's almost there in the photo) I'd suggest keeping your rear foot more over the centerline of the board.
Looks like your heel is much closer to the upwind footstrap than the downwind, and this is causing your board to "carve up" slightly (evidnced by the amount of spray to leeward vs windward).
The "too low boom" is evidnced by the amount of bend in your back arm.
At the point you are ready to go for the rear footstrap, you need to have as much of your weight as possible on the rig through the harness and lines. With your boom low, you are putting too much of your weight on your arms vs on the rig via the harness.
It may be just the timing of the photo, but work on keeping your board very flat (rear foot over the center line so you can toe/heel steer)until you are fully planing.
Hope this helps,