1 - Breakage HappensFirst off, remember that breaking skateboards is normal. I know it can get expensive, but it happens, and being muscular or heavy means you're probably going to break a few more than the other skaters. Also, if you are good at skateboarding, you should break more boards. When pro skaters are filming for videos, they usually go through a skateboard every couple of days, on average.
If you are having a hard time with learning to skate as a bigger guy, check out this other skateboarding FAQ - What should big or tall skaters do, when learning to skateboard? It might help more with that direction.
One thing I can say here though is, learn to land with your feet over your trucks. That alone will help a lot. If you do that, and bend your knees deeply when you land, that should save a LOT of skateboard decks.
2 - Buy the BestSecond, make sure that you have been buying good solid pro-grade skateboard decks. They should be from a legitimate company, like Zero, Element, Powell or Plan B. Those are just a few of my favorites - there are piles out there. Check out this list of the Best Skateboard Deck Brands for more ideas. I just want to make sure that before I send you after some odd tough boards, that you have been breaking strong ones, and not cheap knock off or made-in-China skateboards. If you HAVE been riding cheap boards, then give a pro grade skateboard a shot first.
3 - Tough, Strong SkateboardsIf you've been riding good quality boards, and landing correctly, and still breaking them, then you might want to go for something stronger. This should be your third option - buy a tougher, stronger skateboard deck. Here are a couple of ideas:
- Lib-Tech Skateboards - Lib-tech boards are made with a lot of thought put into the technology behind them. They brag that their boards are super strong, and a lot of people agree. One problem is that with all the fiberglass and other things, if you DO break a Lib-Tech board, it's uglier than just snapping a wood board. Plus, wood has a good, natural feel to it. Still, if you and your son want strength, these might work.
- Revdeck Revolution Skateboards - These are made from carbon fiber, and are in fact very strong. They claim to be the strongest on the market. The big draw back that most skaters experience is that they feel nothing like wood skateboards. At all.
4 - Get a JobIf buying a tough or strong skateboard isn't your style, I completely understand. My last piece of advice then, if you don't want a tough skateboard, is to just buck up and buy more boards. Maybe get another job to pay for them. Breaking skateboards is normal, and there are some cheaper pro-grade quality boards you can ride. But honestly, with a little practice on landings, you should be breaking less boards, and be OK. Still, you are going to break your skateboard from time to time.
You can always keep the busted boards, and make something out of them. Hang them on your wall to show off how intense you are. Or hang them from a tree, like the skaters like to do at my local skate park. It's kind of creepy, and cool, all at the same time.
Whatever you do, just remember not to think that being heavier means you can't skate. There are some stocky pro skaters out there, some tall ones, and they all do just fine. Besides, there are plenty of advantages to being larger! Relax, enjoy who you are, and enjoy skateboarding your way.