I have a collection of watches, i try to go for unsual watches. Varying from mid price to actually quite cheap but ones that you will rarely see.
My favs are, my Rolex Oyster (a standard new shape rolex), Tokyoflash dots watch (big and unsual, looks great when going out), an original Klauss Botta Uno watch, (sleak and looks good in a suite), and last but not least my E-ink Phosphor watch (good for something different to wear on a night out)
Just a selection but my favs at the mo.
A watch i find tell alot about a person, and everyone should have a good watch, and a lucky watch! They dont have to be exspensive, and tbh most watches that are exspensive brands i see people wearing i would take a guess 50% are fakes.
The best way t get a small disount on exspensive watched is to buy them in duty free, thats the only place you will get a vague discount on a new Rolex etc..
Personally i wouldnt buy a second hand expsensive watch (assuming its not rare), as i would feel the owner has probably most likely sold it as they have fallen on hard times...and then your going to wear it....
A good watch will last you forever, assuming its well looked after