I am in somewhat the same boat as Belskorpio with lots of sails, but where I sail, there is a 100 meter wind shadow between shore and where the wind begins. No way to take a wind reading, so I have to do it by sight and I sometimes use binoculars to see what's happening a half mile from shore.
Also, all my sails from 6.6 to 11.0 have adjustable outhauls to maximize my adjust-ability. However, they aren't much of an advantage with the 6.6, somewhat with the 7.6 and 8.4, but a big advantage with the 9.2 and 11.0.
Since the winds are highly variable where I sail, I must pay attention to the gusts and not just the average. Average winds may be 20 knots, but a few sustained gusts of 30 can wipe out the forearms pretty quickly so I frequently rig a little small to be sure I don't get wasted too soon.
Life would be simpler with one board and three sails, but not as much fun.
Formula 160; iSonic 111; HiFly Move 105; Tiga 263; '85 Mistral Superlight.
Maui Sails TR 11.0; 9.2; 8.4; 7.6; 6.6; Maui Sails Switch 6.0; 5.2; Maui Sails Global 4.5; 4.0.