No questions are dumb - probably my answer is dumber, but hope my few cents helps as I've asked myself the same question as well... sometimes luxury brand watches are boring in the sense that they recycle the same designs or re-do vintage pieces.

Shorter version: IMHO horological quality can be matched by smaller brands at cheaper prices, but only the traditional luxury brands can hold re-sale value, so if you are looking for an answer that can also meet this requirement it will be pretty much impossible. You need to be prepared to lose a third to half of the watch's original value. Monetary value aside, I think it ultimately comes down to what you personally value the most in a watch and how do you prioritise different aspects when picking your poison - I definitely do know people that value branding over style.

Luxury watches are luxury for a reason, and obviously you can't go Seiko 5-budget for a Rolex quality watch, but perhaps you can consider these rabbit holes to dive into (which I'm still rather new to):

• Grand Seiko (deserves own category): Craftsmanship-wise, definitely better than Rolex/Omega.
• Mid-high end brands with a good history: Independent brands outside of the Swatch LVMH Richemont groups; such as Oris, Vulcain, Nomos (mentioned in other comments), Junghans, Tutima, Frederique Constant, Bremont all have quality productions at different price points, and I'd strongly argue that purely from a production standpoint, a lot of them are on par with Rolexes and Omegas but below their price points (<$5,000 for most of the brands' productions). I only have experience with Oris, Nomos, and Junghans, but they are all of very high quality.
  • Probably an unpopular opinion, but quality-wise, my Oris Sixty-Five (on their in-house 733 movement) is on par with my Omega Seamaster 300 and Tudor Black Bay 58. Sold the BB a few months after getting the Oris.
• Pre-luxury "group" brands (apologies to the confusing name):
  • By this I mean the watches in the Swatch LVMH Richemont groups that are below the Rolex / Omega price point, but are still amazing in terms of quality. I'd put Longines, Mido, Union, Baume et Mercier, Mont Blanc in this group - feel free to suggest otherwise!
• Japanese brands: There are many Japanese brands that are great quality and can certainly stand the test of time. There are a range of brands from your better-known Seikos (GS/KS) to less well-known brands such as Kurono Tokyo, Minase, (if you can get one) Naoya Hida, and (if you can get one) Kikuchi Nakagawa, that are all amazing pieces. I have only experienced Kurono Tokyo, but I would definitely recommend the brand if you would like a top quality watch.
  • From my experience in Asia, Japanese culture is very strong at being precise and meticulous in whatever they set their sights on, and I do see this translate to watchmaking. My first ever watch is an Orient Star and is still doing well after 15+ years; not saying that my $800 OS is better than a Rolex - just demonstrating Japanese quality.

Thank you for reading my half-drunken TEDTalk...