@BadWolf I never rode more than two. When ever I sold one I bought another and it went like that for about a year till they caught up to production and I couldn't do it anymore. So yeah... Never rode more than two before I sold one and started the process all over again... It was fun for awhile. Didn't make a ton but I did manage to pretty much pay for the two boards I own in profits. So yeah... Agree you don't need more than two.
So far I've been lucky (fingers crossed). I've left it locked up outside several restaurants while I eat, with no problems. This was in high-traffic areas where someone carrying bolt-cutters would certainly attract attention, and not for more than an hour or so. Also I'm sure @AdamDoubleG is right--no thieves probably know what the heck this thing is yet, much less what to do with one if they were able to get the lock off.
@Count to add on to what @njcustom said I have had one experience where I was on an extremely rocky offroad trail and somehow a very large rock stuck to the wheel and the wheel tried to keep spinning but the rock was digging in to it and eventually jammed. So it threw me about 5 feet in front of the board. If the tire had treads I could see this situation happening all the time. Just like your car tires pick every little rock and pebble up.
@Wakeboarder54 Ah so that could be a difference between the US and Canada then (or between different insurers) as in Canada you can pretty much schedule anything you like (subject to the agreement of your insurer) as long as it has an agreed value. I have scheduled bikes and other sports equipment and all I had to do was provide a copy of my original receipt which serves as the agreed value in the event of a loss. Either way as you say it would be covered.