Fly at the level you are comfortable with. Don't let anyone push you into flying if you don't feel up to the winds that day. It's your plane and your fun.

$100 used to be a lot to me too. Don't let it bother you. Not everybody has money to throw away just to impress someone, or to fly like everyone else. Believe it or not, but the more experienced guys will respect you more for sitting out windy conditions more than if you took off when it was foolish for your skill level. No shame in knowing your limitations. I've only got around 150 flights myself and I remember how it was to be in your position not long ago. I thought twice about the winds this past Saturday. It wasn't terribly bad, but I waited a while before flying. I don't worry what others think. I could have flown in the wind without any problem, but I wouldn't have enjoyed it that much with the plane I had that day.