I found the best list yet of decluttering questions on Pinterest the other day. They are from The Red Chair Blog and you can get a cute printable version here.
I'm going to list them out though because I think they pretty much cover the hard decisions.
Do I love it?
Is it useful or beautiful?
Did I choose to bring it into my life?
Would it be hard to replace if I needed it again?
Do I need to save it for tax or legal reasons?
If I were free from guilt, would I still keep it?
Have I used it in the past year? The past 5 years?
Does it fit with my vision for the life that I want to lead?