Buddy of mine got one, I swore I would never, then on a big day, unsurfable on anything else, he was outside riding the bombs no one else could get. As painful as it was, I threw down, and no regrets. It's opened up a world of fun that is otherwise impossible. I could have spent the same $ on a jetski and towed in, but then need a team and the logistics/coordination are just not realistic around here....so now I have my own personal tow-in. I justify it as "motorcyle money", as loads of regular folks buy that or an ATV and no one calls that crazy...this is the water version.
The flat water does get boring quick, unless you have new terrain to explore (roughly 25km range). But I never get tired of the waves, ranging from hanging around outside the marina or ferry terminal poaching wakes, to wind swell downwinding, to being out in mysto peaks that aren't surfable.
Buying the name brands is safest. Prices are coming down used. There are also more competitors in the middle range. Avoid the low end, you risk throwing your money away on junk.
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