Given that most of the shortcomings were due to functional/structural aspects, I would probably refrain from buying online if it’s not absolute love where you don’t care if it’s impractical, you have to have it.
This means the question is how much do you love it? Generally, if I’m waffling, it’s either because I’m pushing the boundaries of what I want to spend or because I don’t love it enough. If it’s the latter, I say no. There will always be another bag to buy.
Honestly, though, it’s an ever evolving process for me. There’s been trial and error and bags given away with the tags still on, but all of those were lessons learned and I wouldn’t change any of it because I love the collection I have now.
I think you summed it up pretty well - all my handbag mistakes have been functional/structural problems. Now, the more I look at that shearling bag the more I am certain that I won't use it enough to keep the cost per wear down. I am glad I have all you tPFs, so my temptation gets to slow down. I like the bag, but I don't love it. Honestly, the most used bag in my collection is my LV Neverfull because it is light weight and I am not afraid to use it in the rain. It rains a lot in my city (which a shearling bag seems even more impractical).
So true, it is trial and error process and this is even more so when shopping online. In the past, I had given bags away to my family. Selling bags that I don't use is the most difficult thing.