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boardsurfr said..
Sue, I understand why you are thinking about a leash. I have been separate from my board twice. First time was after a jump with an involuntary nose landing, where the mast foot released. By the time I realized that what had happened, the board was so far away that I had no chance of catching it. I ended up swimming to shore with the rig, which took about 45 minutes in onshore swell. Fortunately, this was on Maui, with warm water and other sailors around who checked on me, but could not get to the board in time. When later walking along the shore to look for the board, it seems everyone knew where it would end up - on the other side of the harbor. Apparently, board separations are somewhat common on Maui.
The second time was on a longboard, when the sail landed on top of the board after a crash in 20 knots. I immediately realized what was happened, but still had no chance of catching the board. Part of the problem was heavy winter gear - a fat wetsuit, boots, gloves, and a life jacket slow you down a lot. Similar to you, I was also recovering from a longer bout with a virus, and not 100% fit. The sail eventually dropped into the water, but the wind and chop still carried it faster than I could swim. Despite being just half a mile from shore and side-on wind, I ended up with a 40 minute swim in 10 degree C water before being rescued - first by my wife (who almost had a heard attack when my board arrived on the beach without me, and had to re-rig to go look for me), and then by the harbormaster and local fire fighters.
I had seen someone else have the same problem with the sail on the board drifting away before. Thanks to shorter boards, this usually does not happen, but a cammed sail floating on the water could be similar.
With respect to using a leash while windsurfing, I don't think it would be a major problem if you never tack. After all, wingers use board leashes all the time. However, you definitely will get yourself and your gear tangled in the leash from time to time, and especially at the beginning. Also, you mention chop hops and bailing out as a reason to consider a leash, and that the one time where you absolutely do not want to be leashed to your board. If you and your board separate in the air and are connected by a leash, there is a very good chance that the leash will pull the board towards you. The board or fin may hit you in the air, or fall on you in the water. In winging, none of the wingers who go for high jumps and tricks in the air use a leash for this very reason.
If you would decide to forget about chop hops and use a leash, always make sure that you have your arms in front of your head when re-surfacing after a crash. There's a good chance that the elastic leash will pull the board towards you, and that it will hit you right in the face as your head emerges. Using a coiled leash attached to the harness seems to make this less likely (compared to a straight leash attached to the leg), but it still happens.
It's made for an interesting discussion.

I only wondered from a chop hop perspective. It's a pity that most of the places I'd be considering trying to jump are cross shore or side offshore.
If they were onshore I wouldn't have to worry.
I'll probably forget about jumps. I think of them when I'm overpowered and you are trying to stay on the water but realise trying them then is asking for trouble.
Feedback has been interesting.
Yes I find swimming with an impact vest, harness , camelback, helmet, gloves and booties almost impossible..