Look, a bag will never make you happy, with what you describe the reward is even bigger because you make a bargain, the odd seller who found something in a thrift shop and doesn't know what they have. Don't laugh but the things in my wardrobe I cherish most are bargains and steals, makes it so much more valuable to me, so much more attached to them than items I paid full price for.
Being able to afford a fabulous bag, great, but again. that quick fix does not make your life better, if you lust after a particular bag, nothing wrong with it, really, lusting after luxury items pushed me to do well in university and business, but at the end of the day they are just that, luxury items. The 1st
Prada wallet I bought as a student, from an outlet, doing extra shifts waitressing, it meant so much more to me than any bag I could afford, I cried when it was stolen (after more than 10 years of wear), not because of the money I had in it or the hassle of replacing the cards, just the sense of achievement and that I had a real Prada item and paid for it myself, never bought simply another one, as it would not be the same (though a fab wallet).
Bags and such are nice, but they are just the icing on the cake, if your life sucks no bag on earth will make it better, if your life is good, that bag is just another reason to smile, basically, as well made as they are, as beautiful as some of them are, as high the prices the designers slap on them, in reality they are only worth what somebody is willing to pay for them.