I've always loved the top one. It is adorable and classic.
I am the opposite. I get extra enjoyment out of bags that I felt were bargains. It is comforting to know that when I get tired of them, I can always sell them and not lose any money. Once I bought a Gucci Jackie on ebay, thinking I was really going to love it. I carried it once and hated it. I'm so happy that I didn't buy a brand new one at the boutique and then find that out.
I totally get what you are saying!

I have never purchased an expensive bag without seeing it in person first. I will usually "visit" it a few times in person and since I have "extensive handbag purchasing experience"--I am certain that is a resume bullet!!

I usually only buy higher end bags that are classic designs or colors--and i don't usually buy "trend" bags that will look dated in 5 years.
With bargain bags I go a little crazier--I'll buy more trendy colors and what not because I know I won't feel bad when I move on from the bag.