I really appreciate watches ... in the same vein that I really appreciate wine. Would I purchase a $20,000 watch ... no. Would I purchase a $20,000 bottle of wine no.
I collect wines for my pleasure, which is twofold, firstly, just knowing I have an exceptional bottle of wine waiting for me is a pleasant thought/feeling and secondly and more importantly to consume, spend an evening savoring and enjoying the exceptional bottle of wine.
I collect watches for my pleasure, which is twofold, firstly, just knowing I have an exceptional watch waiting to wrap around my wrist each morning is a pleasant thought/feeling and secondly and more importantly to wear. It is great to walk around with a handmade mechanical/automatic Swiss watch (or equal), and it is fun when people recognize and comment on the watch. My favorite is this very clean Hamilton, white face with blue hands ... no complications ... true onto itself ... it just tells time.
I do like my iWatch, the very opposite of the Hamilton.
Yes collect. Collect what makes you feel good, what brings a little pleasure into your daily life. Once you start looking at watches (or cameras) as an investment, it is becoming a business and you start losing all the fun and enjoyment. Collect what you can afford. (I have some cheapo watches that are unique and very different but have no resale value, but they make me smile in their uniqueness.)