Diablo,
I had a lot of leggy plants that had problems standing up on their own without any wind. Knowing how the wind blows here, everyday at least 5-10mph, I staked just about every plant. Most of them with small 12 inch wooden skewers used for kabobs. They're hard to see in the pics. After being outside for about two weeks most of them were strong enough to remove the skewers.
The ones with the longer bamboo stakes were pretty tall to begin with and wouldn't have stood a chance outside without some type of support.
I don't think it really matters which side you put the stake, with or against the wind. I think I'd place the stake on the side the wind is coming from. With pots it isn't that big of a deal as you can always spin the pot.
Good luck.