It's clarifying to establish criteria by which you're comparing, otherwise, it's apples vs. oranges around and around without end.
There are so many reasons you might value a particular watch. Sentimental, material composition, engineering, history, aesthetic, prestige, community, innovation, comfort, longevity, total cost of ownership, etc... pick one category, and then you might be able to compare objectively.
I've had expensive Patek, AP, and Lange watches; I've had independents like FP Journe, Nomos, and Louis Erard; I've had your mass-produced and bulletproof Rolex sport watches; and I've had my fair share of microbrands, especially Halios. I've liked them all (some more than others, naturally)
Comparing Rolex vs. Halios is a legitimate question, but there isn't a clear cut answer either. My 116600 Sea-Dweller is a keeper because it's the perfect Rolex for me - purpose-made sport watch, relatively niche w/ short production, bit larger watch within the catalog, and a stellar movement. But I bought the Halios b/c I think Jason and Rob are both great friends who I've known for years, the watch is creative and unique, the price point is quite affordable, and the quality for the price is pretty fantastic.
Having owned a bunch of Rolex and a bunch of Halios, it'd be silly to say the Halios was a better made watch than the Rolex - it's not. But it'd also be silly to say that Rolex is a great deal - it's not! It's certainly possible for them to both be good watches simultaneously

As to whether I would still buy Rolex if it wasn't appreciating from MSRP? Absolutely - I bought them more often when that was the case. As they have gotten more desirable, I have actually wanted them less.
I think the independent market is in for a shock. Small production numbers have insulated them a bit from the deflation that Patek, AP, and Rolex have seen lately, but before independents were pumped up by influencers, they were a really hard sell, especially on the secondary market. I'm convinced most buyers are in it for the appreciation and everyone is waiting until the peak of the bubble before trying to get out. I bought an FPJ Chronometre Bleu when it was just over 10k, and I thought it was an overpriced watch even at that.
