When I first started to become interested in watches, $5,000 seemed like a certifiably insane amount of money to spend on a timepiece. Honestly, it still seems like a lot of money to burn on something that we literally do not need (at least most of the time), but, as is the case with so many of us, as we learn more about the history and craftsmanship that goes into a great watch, previously ludicrous dollar amounts become more comfortable, and we start to rationalize and defend that which a previous version of ourselves would have dismissed immediately. 
I absolutely believe that $5,000 is more than enough to build a satisfying collection of watches. You could have a good watch for every day of the week and then some, and likely never tire of rotating through a varied collection for $5,000, or even less. Picking just three watches, though, is much harder, and begs one to really identify what it is that they value in a watch. Chronometric precision, hand-craft, great design, historical significance – all of these things cost money, and the list of watches that check these boxes is vanishingly small at the price points we?re looking at for this particular thought experiment.  So, the rules, as established in previous iterations of this column: there?s no limiting to watch categories here – if I want to choose three divers with the same specs, that?s totally kosher; all watches selected are valued at their MSRP (no benefitting from that solid relationship with...