Hi Dave
Sounds like the Rebel is the perfect kite for you, they are easy to use, comfortable and go upwind easy. The new Rebels 2011 and 2012 models are a lot more powerfull than the older ones, so I'd say if you get a new one go the 12, and if you get another 2008 then get a 14. Also as kites get old they stretch so your 08 rebel will have nowhere near the power of a new 10