A three watch collection question with a twist

I thought this take on a three could be fun to try. Let's see what you come up with. 

First watch: one you could comfortably buy today. 

Second watch: one that's a stretch but realistically doable.  Maybe you've been saving for a year or got a nice bonus at work and want to treat yourself. 

Third watch: completely out of reach barring that inheritance from your unknown billionaire uncle.

Bonus points of the watches aren't already in your collection. 

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Here's what I came up with:

First watch: Oris ProPilot.  I was on the fence between my ball and this oris, the deciding factor was finding the ball lightly used for a great price. 

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Second watch: Cartier Santos XL. I thought these were a bit different until finally seeing one in person. 

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Third watch: Patek Philippe 5711 white dial.  Most likely I'd change my mind after seeing one in person but from a distance they're just cool. 

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Thing is: I don't look at watches that way. Just because I can afford an expensive watch does not mean I will. Two issues: (1) I do not see the value that high-end watches bring; (2) I like to mess about with a multitude of watches, buying sometimes 4 watches a month, and 4 watches the next month. That I could not do even with watches like the Sinn 556, the watches have to be dirt cheap for that game.

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Category 1: a Sinn 556

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Category 2: a Lange 1

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Category 3: one of those Patek Philippe with all the trimmings.

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My picks are currently 

  1. IWC PILOT XVIII 
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2. Cartier Santos gold/steel medium

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3. A Lange & Shone, Lange 1 perpetual Calendar 

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Interesting. 

1- Cartier Santos (medium)

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2- Rolex Pepsi GMT

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3- 

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1.  PRX 

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2. Tudor 1926

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3. A Lange & Sohne Zeitwerk striking time 

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  1. Cartier Solarbeat
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2. Jaeger LeCoultre Reverso Art Deco 270.2.62

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3. A. Lange & Sohne Zeitwerk Honeygold "Lumen"

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I like this game...

Serica 4512 Commando 

Omega 300M Blue Dial 

A Lange Sohne Datograph Perpetual 

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I think a nice colourful watch could be fun to add.

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Definitely would not mind saving up for this watch.

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This. This is art.

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And now you're cursed as I am lol

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First watch: Seiko SPB143. A great everyday go anywhere do anything type watch.

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2nd watch: Cartier Santos. For those times when you want to ride the line between dressy and casual.

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Third watch: I've always pictured my grail watch or watch I couldn't imagine spending a ton of money on to be a precious metal dress watch. So after some browsing because ive never really thought about it before, I landed on the Vacheron Constantin Traditionnelle Complete Calendar

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  1. Hamilton Khaki Field Mechnical 
Mechanical 38mm

2. Rolex 126711CHNR Rootbeer

Rolex GMT-Master II 126711 CHNR Two-Tone Root Beer | REVIEW

3. Grand Seiko SLGT003

Introducing Grand Seiko Kodo Constant-Force Tourbillon SLGT003 (price)
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O&W P-101S

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Tudor Ranger

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Omega Aqua Terra GMT Worldtimer (I know, it’s not billionaire tier, but I can only go so far)

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Assuming retail, unless specified 

  1. Sinn U50 SDR
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2. Rolex GMT Master 2 Pepsi - 16710 (grey market) or 126710 (image courtesy of Time and Tide)

Rediscovering The Rolex GMT-Master II 126710 BLRO “Pepsi”

3. Lange Datograph in Platinum

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