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For your son you might consider leasing equipment at the beginning of the season, especially if you think he will outgrow it in a season. Instead of buying off eBay you could also go to the ski and board swap meets that most ski areas have in the fall before the season starts.
I have never skied but I've been boarding for a few years now and talking to friends most of them say that boarding can be more difficult to learn but it is much easier to become proficient. I also think as a general statement that i see more snowboards falling than I see skiers falling. The only explanation that I can think of is that you have more edges on skis than on a board and thus a better margin to save yourself. Thankfully it appears to be much easier to get up from a fall on a board than on skis.
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