Thanks everyone. It wasn't easy, but here was my thought process.
-First off, I would consider myself a chronic flipper, with nothing staying in my collection, typically for more than 3-4 months so I have owned hundreds of watches, never really exceeding for than 5-6 watches at a time. I have tried a lot.
-I learned over the years that I like dive watches. I like the robustness, water resistance, the look, and I always reach for them when choosing from my watch box. Business casual at work, so never had the feeling of needing something dressier.
-I started with Seiko and micro brands, moved up in value including tons of Omega (Speedmaster, Aqua Terra, many Seamasters, many Planet Oceans) and Tudor (Black Bays in all colors, Pelagos in both colors, Heritage Chrono in all colors), stopping at the highest end and priciest for me at Rolex, (Sub, Explorer, both colors of the Explorer II, and a Datejust II)
-Came to the conclusion that the two brands that I loved wearing the most, brought me the most pride, and struck a balance for me between prestige, enjoyment, and value were easily Omega and Tudor.
-3 watches total would probably be my ideal number, but after selling everything off, 2 seemed right to get me what I was looking for without dipping into my checking account and just using watch sale funds for the new purchases.
-I was initially going to get one Omega and one Tudor, but the Planet Ocean and the Seamaster 300M were my top two choices, with the Pelagos a close runner up.
-For those that were asking, these 5 watches were my most recent over the past couple of months that made the sacrifice to get to my two.