Hey Tim!
I am a newbie myself, but I had a lot of help from an experienced kiter when it came to hunting down second hand kites.
Questions you want to ask when buying second hand are
-are there any pinholes, tears or other damage (such as wear) to the kite
-how much has it been used
-all valves sound (not leaking). you could ask the person to pump it up, leave it over night and then conclude if the pressure has dropped or not
-first owner or not
-what conditions are the lines in
-does it come with a bar/pump
-why selling
also remember, that when buying second hand through a shop you sometimes can get warranty on the kite (e.g. if it is an ex demo)
I was also advised, that if buying privately, and the kite you get is not as described, you have some protection under the Trade practices act and consumer law (entitled to your money back)
as I am new to this as well I cant comment very much on other kites, but I hope this info helps you a bit in the process
happy hunting!

elise