big plus one from me to both.
so ive been mulling over my question, and its really hard for me to say definitively, but i think if i am being honest, that if i took a less OCD/watch nut approach to buying watches i doubt id have all the same models i have now.
my first two models were bought before i got in as deep into TWAT-ness as i have since then.
first i bought an ebel 1911, big date. i bought that watch 100% based on looks. i wanted a watch on a brown strap. with an exhibition back, in the under 2k range. i think i paid 1700 or so, maybe a little more.
then about a year or so later i decided i had to have a rolex. i got the 16220, oyster band DJ, white face RN. i loved that watch. (ill not talk about selling it because that story makes me teh sad). i bought it for 3 simple reasons. i wanted a rolex, i loved the look, and it was at a price point i could manage.
after not too long, even though i liked the look of it, and ebel is not a bad way to go, i decided i wasnt enamored with having an ebel, so i decided to sell. at this point i was a certified watch nut-job. i got about 650 on ebay for it, after fees maybe 500 or so. pretty much took a bath, and it didnt feel great, but at least it was on a smaller ticket item. it was then that i bought the JLC squadra. i bought that watch for a great number of reasons, all of which i have enumerated here before, and i can confidently say that even had i been in the market as a non watch nut, that i would have bought that same watch. i loved the look, and still do, and would not have cared about resale. (lucky me the watch has literally more than doubled in MSRP since then, and i got it at 10% over AD cost at the time, so i did ok there).
from there my next watch was the panerai. i love that watch for many reasons, but if i am going to be completely honest, there is no way i would have ended up with it if i wasnt an enthusiast. its a cult kind of brand, the movement is nice, but not breathtaking , to behold, and its pretty damn big. and on the simple side. if i was just in the market to spend under 5k on a watch, i think id have probably ended up with something else. but on the other hand, if i wasnt a watch nut, i probably would not have been adding to my collection at all, as i was still mightily pleased with my JLC.
my last purchase was the ToG. i think that had i not bumped into it at work, i would never have bought it. i would not have thought to seek it out, and as a discontinued model i never would have found it at an AD. i think i definitely would have bought another rolex, but it probably would have been an updated DJ.
i am definitely happy that i am the watch nut that i am, and that i take in all the necessary TWAT considerations before i buy (the very ones you have all mentioned so far), and i could not be more pleased with what i have. but if i took all that away, and was just out for looks, i would probably have the squadra and a stainless steel DJ or maybe a sub.