Should it Stay or Should it Go

Does anyone other than me find it hard to not love and keep everything they find?  This is becoming not so much an issue for me, but something that is a growing concern in the dark cracks of my brain.  What if as I thrift and junk, it becomes harder and harder to put an item in the booth for resale?  I can't become a hoarder because I don't particularly care for clutter (pretty sure my husband is going to laugh at that), but I also come across some really neat stuff that I just am not sure I want to part with.  And who am I kidding, if I'm not careful, I am totally capable of becoming a hoarder!  o_O

Take this purse for example:

It is a darling little vintage Berne of California handbag that I picked up for $3 at the thrift shop a few weeks ago.  It has a great kissing clasp in the center and pockets on both sides of it.  It's a sweet little bag that makes you feel all girly and sophisticated (I currently carry a bag pack with both mine and the Little Dudes stuff if that helps you to understand my thought process there), but it isn't really very practical for me right now.  It is small compared to what I normally use, and the handles are short, meaning that it has to be carried because it is kind of uncomfortable on your shoulder.  So, all of these things would tell a reasonable person to sell it, but what does my brain think?  "No no no, it's great, keep it!"  Shut up brain!  That doesn't help me!!!  Geez!

So what tips do you seasoned pros have for this newbie?  How do you decide what stays and what goes?  I can't be the only one who faces this issue!  

And now I'm going to go party at It's a Very Cherry World because today is REDnesday!!!  Woohoo!!!