I have windsurfed for 35 years, freeride wind-foiled for 4-5 years and started winging about 1.5 years ago. Over that time I have done roughly 30% Wing, 30% Windsurf (wave/freewave board) and 40%Windfoil.
For me the main benefit of winging is that you can flag out the wing and then focus on riding waves. The downside is that it does take time to learn, wings are like paper (they will rip if they touch your foil, and bladders can get punctures) and using board/wing leashes are a total pain.
For windfoiling, I ride a 105 lt Foilstyle board using my standard wave sails (sizes 3.7 m to 5m) and fast free ride foil (850cm^2). For me as an experienced windsurfer/windfoiler, I can turn tighter and drive the sail harder than I can on a wing. Windfoiling does take more commitment because can't flag out as easy and you need to keep even mast-foot pressure from the sail.....but that's also fun too. Windfoiling is also good in really gusty conditions as you can also uphaul and plod in, and windsurfing wave sails are bomb proof compared to wings.
At the moment, I definitely enjoy mixing it up and winging has given something new to learn (which is frustrating but also rewarding).
