I haven't hooked in yet.. but I'd feel reasonably comfortable doing it now that I have a feel for the local wind effects at the beach. I never fully realised how consistent the wind was until I spent an hour riding back and forward through the same piece of beach at speed - it had alway felt gusty, but it turns out that it just consistently blows harder at some points of the beach.
The biggest problem with my current set up is that my board doesn't let me get far enough back relative to the mast foot. To match up with my wave board, I'd need to get my back foot back another 120mm. Obviously this does bad things to your stance, and the balance of things.
On the plus side though, having weight a bit further forward keeps some traction on the front wheels - the same would probably happen with hooking in though, pushing weight down through the mast foot.
I haven't endo'd(yet!). Speed wobbles are an issue to start with, especially with a nasty old flat sail in gusty conditions. Gear carnage isn't too bad - most of the time when I've come off it's been slow, and it's easy enough to jump off and hold on to the boom or mast on the way. Failing that, it's just a case of figuring out how to 'drop' the rig so it lands on the boom rather than diving straight in mast first. Bodily carnage so far includes a smashed toe (mate had a go without wearing shoes, and smashed his toe into the sand mid-crash), a strained ankle from my best wipeout (parachute landing roll is handy!), and a few bruised achile's from stepping off in front of the back wheel, and having it run into the back of my ankle.
If I was going to make a board, I'd use an overgrown skateboard style truck (like the ones on Mike's board) on the back end, and some castoring wheels on the front as well as making the deck longer, and a bit wider around the front straps (currently I don't have a front strap, but mainly because the deck is so short that it's just as effective to push against the mast foot). I'd also try to get the rear strap in line with the rear wheels which would make it feel more like a balanced 'fin'.
I've looked into making something a bit more custom, but the challenge has been finding decent castoring wheels of a suitable size. Castoring front wheels would allow more freestyle style tricks, and also means that the rear wheels don't need as much 'lock' when turning. Dropping the deck down closer to the ground would be good too, but you have to compromise somewhere!
