Thanks for asking. And forgive the long post but I want to properly answer your question.
I think we may not be communicating clearly. Like you, I always buy a bag because I love it and will enjoy it.

I wouldn't consider any bag that didn't meet that criteria. I just also add in other factors such as functionality, fit with my wardrobe, quality materials, style staying power, potential resale value, etc. I don't give a hoot about store ambiance, relationship with a salesperson, sales people giving me perks, etc.. As much as I love pretty things, I hate taking time to shop in malls, stores, etc..

So I'm all about getting the right bag for me at the lowest price possible and the least hassle.
The two things that have helped me get the majority of my money back is I tend to buy on sale or new / like new preowned and I keep my bags in pristine condition. (The latter is easy for me. I don't seem to "wear" my bags. With a little care, they easily stay looking brand new.)
Earlier in my life when I purchased majority contemporary bags, I found that
Coach, MK and Kate Spade bought on sale would sell a few years later (in pristine condition) for that discounted price (give or take 10% or so). And the great thing about these brands (unlike premium designer brands) is they sell quickly! So it was easy to get out of a bag I no longer wanted.
As I've moved into owning almost exclusively premier brands, I stumbled a bit until I found the brands and styles that gave me the best mix of what I wanted which included potential resale value. I found that certain brands have HORRIBLE resale even if I buy them on sale - Versace, Valentino,
Prada, Miu Miu and surprisingly Celine are culprits with pretty bags that I avoid buying unless I see them being in my closet and getting sooooo much wear that it's reasonable I take the hit. (For example, if I wear a bag 30 times, I don't like but don't fret over "losing" $300-$600 on it. I figure there should be some cost per wear.) On the other end, brands like Dior,
Gucci & Chanel have given me great resale when I have purchased them at a good price. For example. I purchased a pre owned but unused pearlized gray lamb medium Chanel flap. I thought I wanted to sell it and listed it on Tradesy. I got an offer that would have represented only a $200 loss even given commissions. Luckily I came to my senses and kept the bag as it's so pretty! LOL! I buy Gucci on sale (40-50% off) and Dior pre loved (50-70% off) so it's not hard to recoup money when I want to sell. I've even had a few cases where I made a tiny bit on the sale. It doesn't happen often but it's fun when it does.
I typically sell on eBay or Tradesy to lessen the commission bite. I've also used Ann's Fabulous Finds for a couple of items. Bottom line, handbags are my passion and hobby. So it's fun for me to hunt a bargain on the bag I love. That being said, I'm not a flipper. I want my bag collection to be stable so I try to buy "forever" bags. But every now and then a bag needs to go and I like knowing I won't take a big loss when it does.