I'm in a similar boat and I find it really hard to talk watches with folks who are experienced in the way of the Rolex AD.
I really enjoy cheaper vintage watches that call back to when everyone had one of them on their wrist.
Something about a semi-autonomous machine ticking away on your wrist, whether you're looking at it or not, using no electricity, is just intrinsically satisfying to me.
I got into watch servicing pre-covid, but never got into actual fabrication of parts. I mention pre-covid because it really got popular when everyone was stuck inside and there was a sudden loss of cheap ebay parts watches to pick from.
Rolex ADs are just a para-social gatekeeper for Veblen goods, but there's a huge resurgence in the entry level Swiss Automatic space with some fantastic value propositions in the likes of the enormously popular Tissot PRX 80 line (hello Rolex Land-dweller), or the more recent output from smaller marques like Christoper Ward who are producing COSC certified swiss-made watches for about 4x markup whilst Omega and the rest are jacking up prices quarter on quarter.
Yeah, it's always interesting when I run into watch guys --- my father's 27-jewel Seiko is too large for my wrist, and the date wheel is broken (and I can't find anyone willing to fix it w/o a donor watch), so I wear quite modest watches such as a Timex Indiglo, or a Seiko Solar --- folks are understanding and sympathetic and almost always have stories about repairs, or watches which they are hoping to have the chance to buy.
I've never owned a mechanical watch(did just recently buy an Orient solar watch after I lost my fitbit while traveling and after a couple weeks, realised the only feature I actually missed was having the time on my wrist), but I like watching the channel Wristwatch Revival on youtube. That guy will often repair old watches that most watchmakers won't touch, sent in by viewers, and make content out of it. And he especially loves taking on watches thathave sentimental value for the owner.
He also recently started a watch repair shop specifically catering to cases most watchmakers won't accept, might be worth checking out.
Tempting, but "Services start at $1,750" --- I could buy multiple replacements for that, or make a downpayment on the Seiko Grandmaster or GPS which I want...
That said, I'll keep it in mind and maybe if I come across a windfall will apply thusly....
Wear whatever makes you happy without apology. Rolex, Timex, Apple Watch. Whatever. I find a large inverse relation between people who care about the cost of the watch you wear and people who are actually interested in the mechanical function of a watch.