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Subsonic said..
For me it's just something that comes from sailing them in different wind strengths. Trial and error (lots of error). Then reviewing what happened on the wind graph afterwards.
Yes
A lot of time on 9.0 and racefoil made it easier to just deal with overpowered situations when using freeride foil kit (slingshot). I worry more at the high end of getting into survival mode but it's not as common here. I know that if it gets a bit lit up on my 6.6 and i76 that I can safely make it back, just point deeper downwind and upwind to deal with overpower with apparent wind or with using the foil lift to push upwind harder. Same with being massively overpowered on a fin but the angles are less (and my experience is now less as well). But the i76 doesn't point as high as the race foil, and it's very noticeable in comparison.
After more TOW I know that if it's not happening with a 6.6 and vigorous pumping on the i76, it likely isn't happening with a larger sail. I don't have a board appropriate for the very aft lift of my i99 so I don't bother now (saving it for a wing maybe). But the 5.0, 5.8, and 6.6 cover me for 90% of the time I want to use freeride gear on a foil.
When I first started foiling I couldn't figure out how to deal with overpower and would limp home by flagging the sail and shlogging back. Getting over that fear and getting deeper angles made a lot of difference, but it wasn't "comfortable".