As others have already mention forget the appreciation aspect. It will help if you can start by doing some looking around on your own and getting a feel for what you like. Some examples:

• Bracelet or Strap?
• Automatic, or quartz?
• Silver, or other?
• Diver?
• Complications?
• Dial color preferences?
• New or Used?
• Chronograph?

Your price range will weed out a lot of options, but there are definitely watches out there you will find. The willingness to look at used will also help, but again, you can find options for new watches in this price rage. Once you have some things you are looking for it will make targeting brands/models easier.

Hmm. Maaaaybe, if you bought like, an old vintage watch in good condition that was interesting in a way that won’t fade away? Like an antique Vulcain Cricket or a railroad-age Ball pocket watch. Other than that, though I think you’re out of luck.

1. Buy whatever looks interesting to you.

2. After you own one watch for a while, consider what you like and don’t like about it, and then buy another based on that impression.

3. Many places sell watches. You can determine if an offer is fair by comparing it to other offers for the same watch.

4. Watch winders are almost never necessary, but you can buy one at any time if you want.

but would like to buy something that keeps its value or even increases (is this even possible with watches in this price category?).

Virtually impossible and on the rare occasion that watches in this category do increase in value, nobody can predict in advance.

The rest of your questions don’t really make any sense because they just treat watches as interchangeable pieces and what you collect is down to your personal interests and style - none of that information is present.

As someone already said. No, they will not increase in price. Price increases happen thru scarcity. But anybody can walk in and just buy a watch in this price range. So there is no reason anyone would pay you more than retail for a used one.

As for what brands are worth it (as in nice and high quality, not as investments) in this price range here are some:

• below that price hamilton, tissot, certina, orient
• around 1k new: mido, some upper tier ones of the above mentioned brands
• maybe can be found new, but certianly used, for 1-1.5k: oris, longines, rado or (with some luck) nomos or even a tudor 1926.

I dont think making a plan ahead makes much sense tho. Your tastes will change with experience, your budget with career advance and level of interest in watches and there will be new releases in the watch industry.

So just buy something you like, wear it for a few months. See what you like about it and what not. Then buy another one and repeat. You’ll build your taste over time.

Also a good resource: teddy baldassare on youtube or his blog has many overviews of different styles of watches or watches at a certain price point. Watch some of that.

Please don’t buy a time peace even a fine time peace with the expectation that it’s going to go up in value you’re going to be disappointed at some point. Aside from the hedge against inflation that it might provide, the last many years have been an anomaly.

I’ve been collecting watches for about 40 years and started off with a Seiko, which wasn’t really much of a collector watch and what I found myself doing from time to time was buying watches that I thought I wanted, but ultimately didn’t, so if I could give my twentysomething self a piece of advice it would be to focus on the best quality watch you can get for the best price.