Loved reading this thread. I personally don't have an already-traveled-journey to share, since I'm new to luxury bag buying.
What's interesting is, before I got on this "journey", I had literally one basic bag which I would use always, even if it didn't go well with my outfit. A bag was an accessory with a function and not really more than that for me. I would annually buy a bag because they would get worn out within a year's use. Money was not an issue, exposure was (I live in India, luxury stores have opened up in past few years).
Until, I bought a small
Gucci bag from their outlet in La Vallee Village near Paris - it was blasphemous, of course, to spend so much money on a bag

, but I convinced myself it would be the only one and that it wasn't even full price. This was in 2017 and that bag is still as good as new inspite of me using it so much.
And now, I am trying to build a functional, small bag closet - previously a foreign concept to me.
Trying to build my bag closet from ground up, posted about it here -
https://forum.purseblog.com/threads/building-a-functional-curated-small-collection.1044580/
Would love suggestions from you lovely ladies, and what you have learned in your experiences, so I can avoid those mistakes early on.