I tried it out whan I lived on the North Shore. My friend had a beginners board and a full range of sails. Took me all summer till I was good enough to enjoy a few of the finer aspects of WSing, and that with a long background of surfing and sailing. Its an awesome sport, or passion if you reach that level. For me it was too equipment and time intensive, especially for riding waves, which is what everyone does here. My biased opinion says go for it!
I've tried it a few times with some friends equipment and help. I think so far my record is about 50 ft of surfing. It's really hard to get that down. but it looks totally awesome once you do. My friends who are good at it can go fast for miles and miles wearing the harness.