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If you buy used most of the better makers will retain most of their value, but a near new or EX watch as a daily will get wear and the price will drop accordingly. Check out timezone's watch rating scale.

You have to choose carefully to retain value...trendy, low prod, color, classic, heritage or nouveau on and on. I still don't understand the prices people pay for unrare, ETA movement Panerais, but they're very popular. But those are $$$ options. Like the poster above, stick with brands like IWC (nice pieces), Rolex, Omega SM at that price.

Check out Tudor, I have a heritage and love it. For the money, a new Tudor is very reasonable and they are beefy. Also a more youthful, less conservative brand than their parent company, Rolex.

However, you also asked about appreciation also, and that's a more difficult proposition.

I think it's safe to spend on large diameter vintage chronographs, vintage Rolex and Patek and of course rare complications like a A. Lange and Sohne repeater...well, brands with years and models that have been market proven for some time.

For what I do and where I live I like vintage tool watches, favorite being a 1680 Red Sub.