This has been discussed over and over in the forum, as you can imagine.
Basically, the resolution is: Handbags are NOT something to "invest" in. Talk to your financial advisor and invest your money wisely, and talk to your best friend about handbags and buy what you like.
Why in the world would you part with your bags now (the bags you say you 'really love') because they may not be as valuable in four years? Are you truly buying bags with the idea that you might recoup their cost? Oh, dear.
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I would never assume bags as an investment. It's just super sad that you yourself will be considered outdated for wearing them since they are 10 years old and it's easy to track when the bag in question was in stores. It's just that even all major bag collectors prefer to go only for lv, chanel and occasionally for obvious reasons - hermes. But that is a smart move
Besides, i love my roady and now i see so may roady's being sold for so little compared to what they were a few years back and people don't seem to want them any longer