RE: When to fly and when not to fly...
Don't worry about not flying, you will find that as you fly and get more comfortable, you will feel more and more confident. When I started, I did not fly in anything over 10mph. That has now gone up to between 15-20mph (depending on direction and gusts), and I am still comfortable. I also gauge the wind against what plane I am flying. I have a 4*60 that came out on the heavy side after I did some modifications, but it still flies great and in a wind it goes right where I point it.
One other thing, the worst you can do is let someone at the field talk you into it. You will get there with time. Once you decide it is too windy, don't second guess yourself. You still gotta land it when your done.