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To the original poster:

I currently own a 94 Four Winns Freedom I/O with a 4.3 V6 and am an avid slalom skiier. My ski partner owns an 05 Outback which I've spent a lot of time behind. The wakes...

I'm not an expert on ropes and handles, but I do have an opinion after doing some shopping at the end of last season.

First, you should have him go to your local boat store and 'feel' some handles...