I'd be happy to donate most of it, but I'd have to sort through everything, figuring out if each thing is worth selling, donating, or throwing away, then figuring out where to sell, donate, or throw it away, then actually doing it.
Anyone who has gone through the process, do you have any suggestions?
figuring out if each thing is worth selling, donating, or throwing away
You're already overthinking it. The objective here is to simplify your life, not to maximize your income from the shedding operation or find the most appropriate way to donate something. If that has a monetary cost in selling something too cheaply or donating something saleable, that's the cost of hoarding things you don't need.
First, look around you. If, for each thing you see, you can't immediately say why you have it, it goes on 'get rid of' list. This means you'll get rid of something you'll need later on, most likely. That's okay. Rebuying something will imprint in your mind why you need that thing.
Sell anything obviously saleable and big ticket. Couch, computer, bike.... anything that can go quickly on Craigslist for a chunk of cash to the first person who says "I'll take it". Price it to move, not to get rich. Remember the objective.
Donate the rest. Places like the Salvation Army will take a lot of different stuff, and you can just dump it on them. Googling your local recycling or donation centres will give you some more answers. Remember the objective.
Throw out the rest. Again, you'll likely find yourself throwing out a lot, and feeling bad about it. That's good, because the next time you're in a store trying to talk yourself into buying something, you'll think of that huge, wasteful purge, and wonder if this thing you're thinking of buying will be part of the next one. If it's not immediately obvious why you'll keep it around, don't buy it.
Go through a couple cycles like this, and you'll have a lot less stuff around, you'll know why you have the stuff you do, and you'll feel a lot less encumbered by possessions. Also, remember that this doesn't have to happen all at once. Every Saturday, find a bunch of things to donate or sell, and do it. Every Friday night, throw out several things you don't want. Eventually it becomes a continual, easy pruning process, which is ideal.
Go to your closet and turn all of your hangers around backwards, so that the tip of the hook is facing you. Go do it now. Also, add a reminder in your calendar for one year from now.
Now, each time you wear a piece of clothing, when it goes back into the closet, put the hanger in normally (tip of the hook away from you). When your reminder comes up in a year, donate to charity any piece of clothing that still has a backwards hanger.
If its something you think you should have used during the year (not long term keep sake or legal documents), then figure out what your going to do with it. Don't do everything at once. Just pick some stuff out of storage and determine what to do. Slowly.
If you need it, just grab it from storage. If nothing else, a storage garage makes a fine place to keep your encrypted, backups.
[edit] put Rubbermaid shelves (or equiv) in the storage garage, do not pile boxes. That will defeat the purpose. The Rubbermaid shelves are easy to put up and sell / donate later.
I like the Rubbermaid shelves idea though.
They go up/down quick, hold a lot of weight, and last forever (easy to sell to the next person).
I was traveling and in the meantime let a friend stay at my apartment. For this, I moved all of my belongings to the basement. After I returned, I shared my apartment with another friend. It was small and quite full, so I only took back the bare necessities from the basement. At some point I noticed that I had taken all that I needed from the basement, and that the rest was mostly unnecessary. So every once in a while I go to the basement to take out some things and throw them away.
The good thing about this approach was the following: Don't go through your stuff and think what you can throw away. Assume that you want to throw everything away and pick what you want to keep.
It's much easier to decide to keep something than to decide to throw something away.
Donate everything else to a good charity. Especially the valuable stuff. (Assuming you have good finances and don't really need the money)
No exceptions.
Emergency Supplies.
Gifts.
Medicine.
Pokemon cards.