in my humble opinion, when, say, drifting with a current on the wind, 100% of the time I am jigging on the WINDWARD side of the boat. The side that is closest to the source of the wind/breeze. That is your face would be into the wind while you fished. This is primo jigging technique and if the wind and current align, you are off to the races! My lord what a perfect dream, jigging a Parry Sound District lake, wind in your face, 1/8 oz doing her thing with the "lift and drop"....heaven!
Fishing the LEEWARD side has some problems. you can't of course drift jig because once you cast you will soon be on top of your lure. There is a fear of hooking a fish and then it is under the boat fighting as you drift over it and it ends up on the other side of the boat. Even working a plug or spinner etc casting into the LEEWARD side means you have to retrieve that much faster before you are on top of your lure, and that makes life difficult as you will not have a correct handle on how fast your lure is being worked.
In very shallow water where the fish are shallow, fishing the LEEWARD is a benefit because those fish have yet to see the shadow of the boat pass overhead and all the problems that can pose that will spook them. Sometimes in a crowded boat someone is left to fish the LEEWARD side lol poor guy.