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What I have (or is on the way), three watches, under $1000, total:

Seiko SKX173 on Miltat bracelet -- mod parts on the way: Dr. Seikostain bead blasted coin edge bezel, Dagaz 12hr insert


Seiko SARB035


San Martin Pilot, 39mm, bronze


Where I might like to end up:

Halios Seaforth w/ 12hr bezel


Orient Star Seeker GMT


Sinn 556A


Honorable mentions might include Longines Conquest GMT, Damasko DS30. I like those Weiss watches...

And if it were not limited to $1000/watch, but $3k total, it might look like:
Seiko SRPC39 Mini Turtle
Seiko SARB035
Sinn 6060
 

Attachments

For dress I’d go SARX055 for the diver a Steinhart Ocean 1 Premium (blue) and for a pilot a Laco Munster or Aachen (can’t decide).
 
I think I'd go this way
Sarx055 - dress
Sinn 556 - casual
Random Seiko chrono (I'm clueless about chrono in this price range)
Gw5000 - beater

Personally I'd replace the chrono with diver,to mix things up a bit I'd pick Orient diver

If I do it my way with around 3k budget:
Seiko SBDX011
Original cocktail time
GW5000
 
What is the "Perfect" (Affordable) 3 Watch Collection?!

First, go for ONE really universal watch.

2 universal watches:

Eterna Kontiki

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Damasko da37 or 373

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THEN, you could add GShock or an Apple Watch for more adventurous activities.
So I had the above 2 already: a truly edc watch and a sporty/holiday watch.
I will now add a third one - a weekend/going out watch that is characterful. This would probably be a dive watch or a pilot watch or a racing watch, whatever is your secret fantasy (or real hobby).

I would suggest one of these character beasts as a 3rd watch, esp since the previously suggested Damasko is already pilotish.

A Seiko Tuna, quartz like the original. Undestructible and looks awesome on all kind of straps.
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a funky Rado Diastar Diver, there is nothing like it and it oozes quality.
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Alternatively, a cool vintage watch as a 3rd option. Many, many cool choices. One of my fave ones is this 1960s Rado with lovely markers.

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for me 3 out of these 6:
LONGINES HYDROCONQUEST / ORIS AQUIS / ORIS SIXTY FIVE / LONGINES CONQUEST / ORIS BIG CROWN PROPILOT / SINN556
 
Let's start with the one that would get worn the least: The Dressy One (Hamilton Jazzmaster Viewmatic)


Next, The Beater/Grab and Go (Victorinox INOX V)


Finally, The Everyday (Jughans Max Bill)


Thanks to some good eBay hunting, I bought all three for around $1000.
 
Here is a twist on your $1000 budget. I know you said each, but here is a really nice list of quality WIS approved affordables you can buy for 1K total... with a 4th as a beater to boot!

1. Orient Bambino - Dress
2. Glycine Combat Sub - Diver
3. Hamilton Khaki Mechanical - Weekender
4. Casio G Shock - Beater
 
Here is a twist on your $1000 budget. I know you said each, but here is a really nice list of quality WIS approved affordables you can buy for 1K total... with a 4th as a beater to boot!

1. Orient Bambino - Dress
2. Glycine Combat Sub - Diver
3. Hamilton Khaki Mechanical - Weekender
4. Casio G Shock - Beater
Costco has quite the deal on a black PVD Glycine combat right now for $279
https://www.costco.com/Glycine-Comb...lycine-Combat-Stainless-Steel-Case-Men's-Automatic-Watch.product.100454636.html
Even for non-members, the additional surcharge is about 15 bucks. Still makes it the best deal around on one of those.

In the past, Long Island Watch has had discounts on Bambinos around Black Friday. Might happen again this year.
 
Costco has quite the deal on a black PVD Glycine combat right now for $279
https://www.costco.com/Glycine-Comb...lycine-Combat-Stainless-Steel-Case-Men's-Automatic-Watch.product.100454636.html
Even for non-members, the additional surcharge is about 15 bucks. Still makes it the best deal around on one of those.

In the past, Long Island Watch has had discounts on Bambinos around Black Friday. Might happen again this year.
The Glycine Combat Sub is a must on any list of affordable watches that punch WAY above their current price. The GCS at under $300 is incredible. If you have ever held a GCS in your hand you know that the build quality is superb. It is much better than many divers going for ten times the price. Sporting an ETA 2824, this watch is a monster deal right now! With the OP's budget of 3K for three watches, that opens up an additional $700 to throw at the other two watches. Run, don't walk, to Costco and grab one before the word gets out and they are gone!

 
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My current 3 watch rotation:

Seiko SARB033
Seiko SKX007
Casio G-Shock DW5600


I don't know that I need anything else.

I also have an Invicta Pro Diver 9094OB and a Timex Easy Reader T20041, but they don't really get much wrist time anymore. They're also too cheap to be worth the effort of reselling, so...
 
I'm more on the affordable side:

Here are the ones I own and are currently on rotation

Beater: modded SKX009
Casual: Hammy Khaki auto 42mil
Dress: sarb035/sarb033
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