I can't speak for the one board sailors other than they probably don't consider it to be fun on something bigger, so they try to make the best of it in marginal conditions.
For us multi-board sailors, we occasionally choose a board that is too small, thinking/hoping that there is enough wind to get planing. We do this because the smaller boards (& smaller sails) are generally more fun if there is enough wind.
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.