I guess I have a split personality based on your two rationales.
Rationale #1 - (or bucket #1) I play often and aggressively at the Casinos in hopes of pulling off something extraordinary.
Rationale #2 - (or bucket 2) Is my won the game money so I'm far less aggressive with my money and have gone mostly all in with CD's.
As my time horizon continues to shrink (I'm not getting younger), I'm thinking more about moving some money from bucket 2 to bucket 1... But so far, I'm okay with with things as they are.
Being a gambler myself (but clearly not at your level) I've noticed that losing money gambling hurts a whole lot more than losing it investing. Same goes for making money. There a huge rush getting a jackpot that's just not there when you make money in the market. There's a mental aspect to it where casino gambling has a multiplier effect where you get to live in the moment rather than always planning for the future.