I just looked at the historic wind data for the La Ventana sensor on ikitesurf. There are some days in Oct that look good, mostly toward the end of the month. Looks like the safe months, the months with very consistent wind day after day are Dec/Jan/Feb/March. When we went in Dec/Jan, the wind came up 9/11m consistently at the same time every day and turned off about the same time every day.
Local Beach: Cass Lake MI Port Huron MI (Lake Huron) Metro Beach MI (Lake St. Clair) Harsens Island MI (Lake St. Clair)
Favorite Beaches: Tawas MI (Lake Huron) Oscoda MI (Lake Huron) Little Sable Point MI (Lake Michigan) The Flats (Key West) Anywhere in Cape Hatteras Kite Beach (Maui) La Ventana (Mexico) Barkers (Grand Caymen)
I went in Mid January for 10 days and kited 8 days in La Ventana. 6 days on my 11m and 2 days on my 9m. Then We went down to Los Barilles and kited the 9th day on my 11m and i weigh 220lbs. The 10th day was a day of rest in Cabo.
If you do go to La Ventana make sure you head up to the Hot Springs! Its great up there. Seemed to be a little stronger wind up there also. If you can get a ride you can do the 7 mile downwinder back to La Ventana.
Hot Springs Tip: If you have room in your kite bag bring a big ass tarp. Borrow a 5 gallon bucket from someone down there (or buy one from one of the stores if you can't find someone to lend you one) Drive up to the hot springs. Dig a big ass hole right near the waters edge using your bucket, as big as your tarp allows (we had a four person hot tube). Dig down until you start to get down to the hot water. You want the tarp to drape down and come up over the top. Then put some sand around on top of the tarp so the wind doesn't blow it around. Then dig a small hole right next to your big hole until you get to the hot water then keep digging down so you can start getting 1/4 or 1/2 buckets full of the water. Pour the water Into your tarp and keep filling it up until you got yourself a nice hot tub. Have a few beers, go out for a session, ride onto the beach drop your board and hop into the hot tub with your kite in the air, have a beer, boost out of the tub and session again. It's awesome!