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I never cared about Rolex. It's a meme for "expensive brand". I find their watches boring. I'm sure they're fabulously made, but they've barely innovated at all in the last 50 years, regarding how they look. Their design language is very consistent, which is great from a marketing perspective, but from the perspective of "I want something different on my wrist," it doesn't work at all. I can look at a watch and say instantly "yup, that's a Rolex design." That's not a good thing.
Also, most of their watches are designed as a tool watch: for diving, exploring, etc. Yet, they make the watch out of platinum and cover it with jewels - I don't care if the fish want me to have a $200,000 watch, they can suck water. Sure, there's a place in the world for a fancy watch. A tool watch doesn't seem, to me, to be that place, so it ends up just looking weird.
There are a variety of other luxury watch brands that interest me more than Rolex, and pleasantly, they're all more available and more affordable. (Except for Vacheron, which is not more affordable, but I expect never to be able to have one of those anyway.)
I don't like to take an automatic or mechanical watch for travel, I've had issues with TSA refusing to hand-examine one and ruining a very nice watch in the x-ray.
I bought a number of Citizen Eco Drive quartz watches for me to travel with, because TSA can put them in the x-ray and they'll be fine. There are 3 - one is dressy, one is sporty, one is casual. I just grab that watch roll and take it with me when I travel. (Actually the sporty one is titanium and is my daily beater, so taking it would be a no-brainer.)
I didn't even bother talking to my father about a Swatch. I knew he'd say what yours did, and I also knew we couldn't really afford it and I didn't want him trying to figure out how to afford one for me. I'd rather have housing and food.
For me it wasn't "all the cool kids had one", it was "all the cool kids could afford one." I didn't like that they were all bright lurid colors, but if I'd found one in a more muted tone or the right bright color, I might have been interested. I like today's Swatches a lot more than the originals.
It was an LED digital Star Wars watch. (LCD hadn't been invented yet.) It was before The Empire Strikes Back, so I think it was christmas 1979. (Could have been 1978, but I hadn't seen SW yet then.) The watch itself was blank, it came with Star Wars stickers to give it personality. A sticker would last about a month. Because it was LED, which used a lot of battery, you had to press a button to get it to display the time, which would be there for about 1 second. Like everything I owned, when the battery died my parents refused to get me a new battery, so the watch got thrown out as "broken". (I wish I still had it.)
I later got a Helbros quartz thing with an un-lumed dive bezel (so it was a desk diver). I thought it was long since gone. I recently found it and thought "I used to like this? It's horrible!"
I respect all of them and they all look like great watches. At that price point, it comes down to what pleases you, of which my answer is the Vacheron. Their watches are more my style, which in a way is sad because I don't know that I'll ever be able to afford one.
Most of my watches are in category 1, and I have only a few watches in category 2. I have one vintage watch that is probably worth more, but it was a gift.