Hi Tyler! Like Karen said, to the best of my knowledge Jimbo's truck stop is only done with cruise director Jamie on the last segment of the world cruise.

I would make sure you bring some type of jacket. This is required for informal evenings (tie is optional) and eating in Signatures. The dress code of the evening is required through out the ship (say for example if you later decide to go to the show, into a lounge or the casino). If you want to eat and avoid dressing in formal wear, you can always eat upstairs in La Veranda where the dress code is always casual BUT it limits your after dinner options. There's also room service.

If I were you, I'd try to find a way to pack one dark suit. I think you'll be happy you did.
The Captain and much of the staff will be changing on Wednesday. After doing the World Cruise (and pre-world cruise) the staff will disembark for a much deserved vacation. Their replacements will be top notch!

I sure hope you enjoy your first Regent cruise! Hopefully it will be the first of many.