Sharing my experience - I don’t think it’s possible today, and I don’t think people are really doing it - even the best guys like Sam and Greg appear to be mowing the lawn at a single spot like Kanaha or Kuau (which is incredibly impressive). Next level down pro and semi-pro team riders are also doing the same thing.
I’m a competitive amateur who does ocean racing and medium sized dw paddle runs. One of the dw runs I am able to squeeze into a weeknight is to upwind from home up to an island ~4 miles dead upwind … which requires 12miles of upwind tacking on a 3M wing. Because the wind gradient changes, I only have about a 50% hit rate on launches making it to the island where I do the drybag packdown and ride back. (A wing any size larger I can’t pack down).
I bought a 4M BRM when they first came out, and sold it after 2 x 15 min sessions trying to accomplish a more elegant and streamlined upwind machine. It just was too sketchy, too difficult. However, 6 months went by and I found myself in LaVentana MX - and two parawing-brained friends were like - “We’re parawinging today, here’s your parawing - we’re going right now.” I did not have a paddle with me, or my downwind board, but I had my standard wingfoil setup. We drove 4 miles upwind, launched the wings on land, and the wade-out was on my good side. I popped up after about 60 sec, and while it was chaotic, got the wing stowed after another 60 seconds, and aced the run. No downwind board. No paddle. Just my 10lb 60L board, so easy to pump. It was a revelation. Nothing had changed except what I asked of the wing (upwind machine → downwind cheat code).
But now the wheels are turning again … and I want to see if I can eliminate wings from my life. I tried again yesterday to see if I could get offshore in 18g25kts, and while I can maintain slightly higher than a reach on my good side, it still feels soooooo weird to try and make it work on my switch stance.
I know it’s possible though … I was recently on Maui on a small foil, and 3.5M wing in 20kt wind. I came across who I think was Sam on the PocketWing (vProto?) - holy smokes. I was able to overtake him in my most aggressive upwind speed-demon wing race stance but it was an all out effort. So the proof is out there, but it doesn’t seem attainable to me today.