Winds out of the SE are typical for the plains in Summer and that is what we found on the TA. I think that the winds are a minor factor in choosing direction of travel for your ride.

I have found that for rides like my TA other factors were more important. For example I like to get the long distance air travel out of the way upfront because it is easy to know when you will start a tour and harder to know when you will finish.

Getting a lot of your mileage in early in the day helps a lot with managing the impact of the winds on your tour.