Piece by piece from affordable is the "best" for learning about watches and about oneself.
Love for timepieces does not come suddenly but through owning and enjoying something "lowly" and learning all about it along the way.
The other thing is, I could not speak for others, when I started I have limited financial resources and it would be impossible for me to stalk after some top price pieces. So it is natural to start simple and move on to the more "complicated".
If I should have all the financial resources at my disposal from the very start I could straight away and go for the best stuff but I would probably lose much in the way of educating myself. In fact I started with second hand pocketwatches and as I understand and appreicate the intricacies more in each pieces that I move on.
Having said that, my preference also changes over the years. My buying desire sort of slows down as I "look" more than buy even though I probably can afford more pricey pieces nowadays. I am sure this change is brought about by my continuing learning from my growing collection. I still love all my earlier pieces and have not sold a single one since I started.
W72