Going into my 2nd season of kiting, I would recommend the following:
1. Hook up with Kitopia lessons at Sherman Island. I did a lesson with them and I learned the Sherman Island area, what to do, what NOT to do, etc. They can also give you input on potential gear purchases when you are doing a lesson with them. They are a great resource. (unsolicited recommendation).
2. Really plan on driving out of your way to go to SAFE areas for learning the first several times out (or even 1st season). Think Alameda.
3. Kind of like used cars - The sweet spot is probably 1-2 year old gear. Get brand new lines and bar.