I hate the gambler in boots. I love the old jaime in boots. This is an older one without the track system, so it's possible once the Jaime went to the track system it's no longer as safe to ride in boots. I weigh 200 pounds and have slammed this board, sometimes I feel like I'm about to bend it in half, have been ejected several times in kite loops, and the inserts have stayed tight the entire time. I say go for it, let us know how it goes. I mean you could wreck the board but that's still better than having to ride the gambler
Or maybe get the Team Series. I like the team series a lot better. Just my preference about boards, I can't ride the gambler just don't like how it rides, feels like I'm slogging on a windsurfer. My friend has a newer textreme Jaime with the track system and I think that board is also a fantastic board for boots, I mean if the track holds, and you can only find out if you give it a shot.
But don't take my word for my board preferences go out and demo the boards! who knows what you'll like. Maybe you'll love the gambler.
Most boards from all manufacturers are strong enough for boots and the manufacturers are usually over conservative about telling people not to ride with them. Regular riders don't stomp the landing nearly as hard as pros do. The only reason I would not suggest trying boots on a board is if the board is too flexible. If the board is too flexy, it bows up and down in the middle like some kind of see saw and is unridable. Boards have to be stiff enough between the boots that there's not too much flex.