drewpweiner said..
I'd love to know how you can travel up wind above 1 kilometer without having to go 100m out in to the ocean in straight cross-shore winds. Sounds impossible.
Tacking will slow down upwind progress, but you should be able to go upwind even with <20m tacks. Some beaches have a reverse sweep just outside the wave zone that makes shorter tacks (<50m) even better than longer ones for upwind speed. In general you should be able to upwind in straight cross-shore at walking pace (keep up with someone walking upwind on the beach) or better.
drewpweiner said..
2: Park car and ride my e-bike up to launching spot. Once finished, drive back and pick up bicycle, backpack and pump.
You could try this in reverse: drop off the bike at the end zone, then drive up to the launch spot. That way you can stow your bag & pump in the car and only expose the bike to theft.
Personally I'm with Gorgo. Going upwind solves the majority of your problems. Even tacking hard upwind between sets should extend your session significantly, or limit the amount of downwind that needs to be recouped.