I read this thread with great interest as a junior to this hobby (and a junior in life, being in my early 20s). It baffles me to hear stories about the watch market 30 years ago since that was before I was even born. However, I think we can safely say that one trend is prevalent: up. The main stream vintage watch market is arguably at its all time high right now.
I can't predict the future but I will share some insights regarding my generation. I grew up without a mobile phone until I was 12 years old (I got it when I went to high school) but technology has strenghtened its grip on society ever since. I can't begin to imagine the technological shock more senior members of society went through. Imagine stating in 1969 that in 40 odd years, computers that were thousands of times more powerful than the computer that landed us on the moon could fit in your breast pocket.
In my direct environment there's a pretty sharp division among peers that I think is a good reflection of society in general, distinguishing three factions:
1. The indifferent
A watch? I'll check the time on my phone, thank you.
2. The utilists
I'll buy a basic/cheap quartz watch or even a smart watch for functional and aesthetic purposes. After all, my wrist does appear rather desolate without something strapped onto it and it is convenient to check the time without having to dig into those jeans pockets to pull out my phone.
3. The afficionados
This is a relatively rare breed with an interest in watches that more often than not does not come on its own. Usually these young men pay more attention to their appearance in general and they are more invested in building a wardrobe of good quality garments, opting for quality over quantity. Watches are a logical step in that process.
However,
vintage watch afficionados are seldom seen. I know of one person outside the community that has a mild interest in vintage watches. Some get their interests sparked due to inheriting a vintage heirloom or because there is a broader fascination for 'how things used to be', as opposed to the technological and ever accellerating era we currently live in. Personally I love the '60s style of watches so naturally that is where the accent in my watch collection lays. But this doesn't come alone. In terms of taste I also adore '60s furniture, cars and clothing. Owning and wearing vintage watches feels like using a time machine to me. Not only is the design more appealing to me (aesthetic reason) but older mechanics never seize to amaze me. I've had both an Omega cal. 751 (5xx family) and a UG cal. 69 microtor professionally serviced and both were able to run within chronometer specs - even after 50 years.
In my opinion the main stream fashion in this era largely revolves around toss-away quality and that is dispiccable to me. I am not much of an environmental activist whatsoever but I like to think that I contribute my fair share to the global efforts by giving vintage watches a second life and by buying quality garments only, aiming for a 10 year plus life span.
Now, back to the topic at hand. I think scores of new vintage watch afficionados discover this hobby every day but this might be at a later age than in their early 20s. This probably comes down to a couple factors: 1) money at hand, 2) time at hand. People in their early to mid 30s will usually have settled quite well, owning a house and possibly having started a family of their own. This slows social life outside of family down considerably. Provided this person has a steady job, it is likely that these are relatively prosperous times compared to their 20s. Consequently, there's an abundance of money and a lack of opportunity to spend it outdoors. Some might save up but others might actively look for a hobby and watch collecting is a wonderful option. Perhaps this is why we see so many people in their 30s around.