Nice and thoughtful way to approach the opportunity. I’m thinking of kiteboarding in light wind as using my 9.4 sail became too taxing physically. I can see local ex-windsurfers well into their 60s riding easy on 14m2 kites while I painfully have to pump my big rig and destroy my joints. Luckily, there’s more than one solution with kitboarding, kitefoiling, wingfoiling, windfoiling and gardening.

Curious to hear how the handling and logisitics of gear is going for you with wings instead of rigs? If I had one complaint about WS it's the amount of gear you have to haul around, especially if the forecast isn't super clear as to what sail you'll use.

Is the wing gear easier?
How long is setup compared to WS?
Do you find that the wings have wider ranges between sails?

A couple weeks ago at Wolf I had a kiter hanging around while I de-rigged and it took me a while to figure out that all the questions he was asking were all leading to pointing out that kiting was easier to handle than windsurfing! Guessing winging would be another level easier without the lines and launching.

For me, easy and convenience has never been my top criteria to select a leisure activity. With my kiteboarding friends, We never talk about how easy it is to carry things around or how quick it is to rig or pump a kit. We have a mutual understanding of our sports and recognize what’s great in each. They also don’t try to “convert” me to their sport and I don’t look down on theirs. Maybe not happening like that everywhere, but it is here at my local spot.

As far as rigging a sail vs. pumping a kite, it is very similar. I’m not slower than anyone rigging my kit.
Advantage goes to kite and maybe wing when it comes down to traveling by air of course. I’m not a Pro (haha!) and I don’t need to take my gear on a flight. If I want to travel to a windsurfing destination, I’ll drive and pack my stuff or I’ll likely find equip for rent.
Also I have more places I can launch from since I can rig and get in the water on tiny places while most kiters need s large beach (not too frequent to meet kiters that know how to drift launch).
As far as the bulk of the equipment: Can’t deny that, but is that really what stays with you and you remember of your session? Ease of transport hasn’t yet been a priority for me. It might as get older and can’t move heavier stuff as well. Time will tell.

If I wanted to switch or add a different sport, I’d do it because either I’m bored windsurfing, or I want to learn something new, or I’m looking to discover new sensations on the water, or I want to taking advantage of conditions or locations that might be more suited to a different sport.

KM wrote: Separate pieces (boards, wings, foils) smaller thus easier to pack, but overall amount of stuff ultimately probably similar.
Rigging a sail faster and installing fin faster than inflating wing and assembling foil.
Range of a wing is highly skill dependent, especially low end.
At equal skill levels, windsurfing is probably safer in most conditions, less likely to require a long swim, upwind walk, or rescue, easier to limp home when wind dies or struggle back in overpowered conditions.

So in my journey to getting up on foil, I conclude that the primary barrier to getting there was caused by my windsurfing background. I had thought that I could learn the sport in less than smooth water due to my water experience, just had to learn to stand up in rough water and be confident in staying upwind. That was wrong. Sailing in completely flat water let the board slowly accelerate under control where you had time to adjust to the speed, reset your balance as the board gradually lifted out of the water with the board completely flat in all dimensions. None of the Youtube videos I pored over mentioned the importance of very flat water (although most of the videos are in flat water, some aren't) in being able to slow down the process of getting up on foil, giving you time to feel what's going on. So you need lots of wind, very flat water, downwind security to learn this sport, not always easy to find.

David Mark wrote:
Very true. For learning, conditions less than perfect makes the experience less than desirable. I tried wingfoiling a couple of times this past summer on Lake Michigan. Wind was good but the lake was choppy with side shore downwind current. I’ve been Windfoiling for 3 years now and thought the wing would be a piece of cake. Wrong. The conditions were so messed up that I was constantly fighting the conditions rather than focusing on managing and understanding the gear. Humbling experience.

11 months ago started this thread, first learning steps in SF Bay area. At end of last season, beginning to get some foil rides but nothing was ever long because of lack of space (Lake Andrea) or super-gusty wind (Montrose). I had doubts as to how much I progressed. I returned to the Bay Area to try again on borrowed gear to see if actual progress had been made. Candlestick Park (site of old Giants stadium known for wind) has flat side shore wind coming off the land, large sailing area, safe downwind area for walk of shame. I had my first very long rides, 1/4 to 1/2 a mile rides in control, varying height, upwind and downwind ess turns, gentle landings. This was followed 2 days later by a punishing day at choppy Marina Bay, lots of big crashes but some long rides too, conditions reminding me of classic choppy side-off Greenwood conditions, except that this was safe on shore winds. I'm ready for the season on the big lake. Pic of Candlestick below.

Also met my brother's new son-in-law, a wing and windsurfing instructor for ABK in the gorge, who gave me some useful tips that immediately seemed helpful. He said keep your head and eyes pointed to where you want to go. That straightened me up. Have your nose aligned vertically above your belly button (I assume normal waistline). That's about how much you want to lean back, just a little bit. To initiate turn, start the lean at the ankles, then gradually upward. Fall like a statue toppling over, that keeps the foil away from you no matter what direction you fall.
He seems like a great windsurfing instructor, a student favorite technique that he teaches he calls "sail-chi." It's a series of sail-handling techniques you do on dry land, improves your sense of sail movement in the wind, the key to any advanced maneuver. He says once the sail moves around properly, the feet take care of themselves.

A nice secondary effect of learning to wing on my windsurfing has been a great improvement in early planing. Getting up on foil requires so much more wind than staying up on foil that you really have to pay attention to factors that will increase your speed. This means looking for, sensing, and reacting to gusts to maximize speed, looking for the best path through the water to maintain speed, and judicious pumping. I still suck at all these for winging. But I have a new appreciation in windsurfing of that threshold where the board reaches the point of least resistance to the water, and how much less power is needed from the sail at that point. You get another round of acceleration as apparent wind gives you more speed until drag reappears.

This is my third year wing foiling and I’m 100% addicted to it. My second year, I started learning how to jump, and the feeling of flying through the air is amazing. I haven’t given up Windsurfing, even though I haven’t done it in three years now.

Short video of me winging back to Greenwood beach 2 days ago, moderate winds that kicked up later in the day and almost blew me off the water with a 4.0 wing.