Count me in if it's not too late!!

Congrats on 50K!  Well deserved for the great content

<500: Tissot PRX, Seiko Prospex solar diver

$1,000: Seiko Prospex Diver SPB (6R movement)

$2,000: Oris Artellier James Morrison

$3,000: Longines Spirit Zulu GMT

$4,000: Omega SMP

$5,000: Vintage Rolex

has the winner been selected yet?

Casio is number one.  Some of the "entry luxury" Swatch brands (Longines, Tissot, Hamilton) can have great value, but only when buying pre-owned/grey market at a big discount from the retail price.  A lot of microbrands lately have been punching well above their weight class as well!