I would think jumping from a 2-channel plane as simple as the Outlaw into a very fast 4-channel plane like the Jobar is way too big a leap. This is like going from a tricycle to a motorcycle.

I'd highly suggest a 3-channel plane like the Slow Stick or Tiger Moth. However, since you're insisting on flying when it's windy, you might look into a Mini Piper or an E-Starter set up as 3-channel.

Just remember, the question isn't whether the plane can handle some wind. The question is, can you?