Tom,
I am an ex-windsurfer myself......and glad I ain't poleboarding any more. Very sound advice by Ivo.
First a question, and then some info. IF you had driven to Holland, 3 to 3 and a half hours, and not found any wind....would you have been frustrated and complained about it, or would you have taken it in stride, hung out on the beach in a "good" mood and shot the shiz with the BRO boyz? that is a very pertinent question when wanting advice on where to go on Lake Michigan on any forcast.......think about it hard and long and be truthful to yourself!!!!!!
Now some info......on a SSW in the Fall, I NEVER go to Waukegan, once it switches SW it is no bueno my friend!! South Haven can be great on a SSW, but if it goes South....no bueno my friend. Holland is the first place on the Michigan side to get a pure South. Hell, when I hit the beach at 8 30, it was 5 degrees offshore at Holland....almost drove to Grand Haven, but I figured it would switch eventually, and it did, and it got AMAZING!!!!
So in all honesty, I thought SH would be good, but Holland better. However it was a "crap shoot" quite literally. The group that gathered at Holland rides together frequently. We make the extra drive to find better conditions, not just stopping at the first beach that has wind.

IF the wind does not cooperate, we drive further or "take our medicine" and make the most of it. That is why we usually hang out together after the sesh as well....to enjoy one another's company....not to complain about the wind that didn't materialize...cause it will come back around the next time!!!!
ATTITUDE matters, and we all get "skunked" once in a while....it's just that it happens less frequently than it used to, cause we tune into the nuances of the lake...AND of course I have some rocks that when shaken seem to call up the wind....some find that a bit odd, but all I can say is that I can't create the weather, I can just influence it a bit!!!
And by the way.....Sheboygs will blow on Wednesday.....put that in the bank!!! Waukegan maybe, but then most will stop there if they go, cause it is the first beach you get to....no matter what is posted....and that is just the facts of the matter!!!!