That sounds like it would be self-defeating. He's throwing money away by having to always pay for new registration and insurance, not to mention depreciation every time he goes to sell.
In California, I could ride year round because I have rain gear. I owned this during the drought so we didn't have much rain to begin with.
Here in central Oregon, because we're on the dry side of the cascade mountains, I only have to park my bike when it snows. They do make snowmobile conversion kits for most dirt bikes but I can't justify spending $4k+ for one and I'm not even sure if they make them for my bike.