Editor?s Note: For this edition of The Three Watch Collection for $5,000, we turn to one of our newest contributors, Tommy DeMauro. Tommy has a deep appreciation and knowledge for a particular flavor of affordable vintage. Think ana-digi watches, under the radar and nearly forgotten references from big brands, and pure novelty. Tommy has a great eye and loves digging into the lost classics, and we?ll be bringing you his practical guides to these unusual watches in the coming months. But until then, here?s his 3 for 5k contribution, which ought to give you a sense of what Tommy is all about. 
As someone who has firmly cemented themself in the affordable vintage market, the three-watch collection for under $5,000 challenge unlocked newfound territory for me.  Only owning watches with an initial cost of roughly $400 or less (before service or repairs if needed), I have no experience with luxury brands or any pieces whose market value exceeds my rather low price point. While the appeal of owning a Rolex, IWC, or Cartier was certainly not lost on me when deciding which watches to choose, I wanted to stick close to my roots and pay my respect to iconic brands often found within the affordable end of the market. Now, before I even begin to unpack my three choices, let me first explain my thought process here. I typically gravitate towards the obscure and unique because of my love for design and expression??why have what everyone else is having" That being said, yes, I am...