1. 5A/5B > jump forward > down A+D as fast as possible. Don't wind down before you jump!
2. http://www.dustloop.com/forums/showthread.php?14170-CSE-Rachel-Gameplay-Guide
Your goal is to safely summon the pumpkin. Use your head and be aware of the opponent's options (for example Hazama or Lambda can shut you down easily even full screen, look for dead angles). More often than not you have to create your own space first by stopping their advance with winded lobelias and iris (use wind smartly, don't overdo it). Don't be afraid to backdash/move with them. Don't forget you have one of the best anti-airs in the game (if not the best). Make them move predictably. Once the pumpkin is out you can summon George safely. In certain matchups he is less useful but he could always save your ass. If both the pumpkin and the frog are out, try 236B+5D to send them the whole package. Hopefully you have some wind left, if so it's time to get in if you manage to make the opponent block George. Else, set up your defense again. On the offense always go for 50/50 mixups immediately, this is your strenght and you want to capitalize on it. Don't rush in with a single wind stock though, because if the opponent blocks it you're in a worse situation. By the way this is far from easy and I wish I could do half of the things I said most of the time. Work hard.
Also, watch N-O.