I personally think that the " step by step " strategy is the best one, and the more enjoyable...
It is the best way to discover your / our taste, what we really want, desire, and it is very educative...
As for a wine, if you begin by drinking your first 1 000 USD wine, what kind of comparaison do you have, if you know nothing about wine???
The " Live " Experience is very important, to make your / our own judgement on horological pieces.
Reading some " experts " point of view is good, but not enough.
You / we really have to try, to test, to feel, to live with these pieces to know if they are made for you/ us...
Upgrading a collection is a passion which leads to learn more and more about watches...and about us, too, our real tastes, desires, etc...
IMHO, of course.
Curious to see what the others think...
Best.
Nicolas