If the spending is for clearly separate transactions, such as your example of shopping at different stores, then that seems like it would be fairly easy to defe

If the spending is for clearly separate transactions, such as your example of shopping at different stores, then that seems like it would be fairly easy to defend. What would be problematic here is, say, buying a car with BTC in multiple "transactions", each of which is individually below the $200 gain threshold. It's really a single transaction taking place: BTC for a car. That could be interpreted as intentionally structuring the payments in a way that obviously works around the spirit of the proposed law.