> Another thing that watch enthusiasts definitely warned me about but that didn't hit me until I actually started using a mechanical watch was just how annoying keeping up with a mechanical movement can be [...]
There are automatic mechanical watches. Together with a watch winder you don't have to worry about winding your watch. But I guess there are none in sub 40mm? Haven't payed attention to the space in the last 15 years.
> Like other analog products that persist in a digital age (see vinyl, print media, and board games), much of the popularity of mechanical watches can be attributed to nostalgia.
In addition to that one of the other big reason is probably that expensive mechanical watches are a status symbol, and are also a decent investement. Patek Philippe, Audemars Piguet, Jaeger-LeCoultre, A.Lange & Söhne etc. hold their value well or increase over time.