The issue here is that different things matter to each person, so our opinions about what we would get might not excite you as much. I'd always go for jewelry for myself (solid gold bangles or diamond studs), and if you go with pearls, I would go with South Seas or Tahitians. Tahitians are larger and their colour makes them more of a statement piece that you might find easier to wear than smaller white pearls.
It sounds like you are most excited about the bag, to be honest, and if that is the case, I think you should get it. And I would definitely get the Chanel in red. It would go well with your style and be more neutral than you might think. I'd go Chanel or Bottega Veneta over LV.
I don't wear a watch, but a watch is a very long-lasting piece if you wear one. My preference would be a mid-size Cartier Ballon Bleu over a Rolex, but brand and style is personal preference.
Congratulations on your upcoming 40th!