I've used a hyper (103 lit real volume) over a period of 3 years. I'm 86+kg and with a large rig it was next to impossible to uphaul, especially in swell. I remember a few very long swims from that period.
Waterstarting will not help if the wind drops to 2 knots and you're in the water. So if you're slogging and the wind is dying (watch it carefully while sailing), do everything you can NOT to drop the rig. You will become more comfortable with experience, but for your largest board + largest rig, it's always a good idea to have some extra volume.