Sell, Give, Donate, Dump?
My first thought was financial. We would sell all our stuff and bank the money for retirement. I thought about a giant yard sale, our lawn and driveway covered with all our stuff and people driving up, scooping up all the stuff, and a metal tin box filling with cash.
Then I considered the logistics of a yard sale.
Everything had to be carried out, then organized, priced, tagged, and displayed. Then there was advertising to be done, signs made and nailed to local trees all over the area. People coming to yard sales always need change, so I would need stacks of singles and rolls of quarters. 
The day of the sale, I’d have to begin by chasing away early birds, then sit in a lawn chair from early morning until we closed the sale down. And if I were sitting out front in the lawn chair, who would be watching all the stuff in the driveway and answering buyer questions such as “What the heck is this?â€
Then, since not everything would sell, all the leftover stuff would have to be hauled back into the garage.
The term “major project†came to mind. I decided that a yard sale was a younger person’s game, not a geezer task. I suppose I could have hired a professional to run the sale and give up half my profits. But that would have required first finding, then hiring a professional with the potential of having him or her evaluating our stuff and telling us that it all belonged in the dumpster. All our great stuff! No way!
So it was on to Craigslist. Take a photo. Do a write up. Post and wait for the buyers to start calling. 
Unfortunately, there are a lot of people who call for stuff, say they want it, and never show up. We soon instituted a “first come, first served†policy. Calls be damned. If you got to our door and had the cash, it was yours.
We sold a dresser, a lamp, and some books. Everything else quietly expired after 7 days on Craigslist. We still had lots of stuff.
Now it was time to invoke the best sales word ever invented – free. We again listed on Craigslist, but this time it was the free section. We had to face facts – there’s a lot of stuff people just don’t want to pay for – no matter how valuable we thought it was.

Free stuff began moving out the door at a rapid clip. Old lamps, end tables, chairs. All gone in one day. People even asked about other stuff they saw when they came to pick up their stuff. That old chalk board? Sure, take it. That white bookcase leaning against the wall in the corner? All yours.
We even had a set decorator for a low budget student film fill her small car with all the old wood we had lying around the garage. Zombies were going to be tearing it apart!
The big stuff was going. Now it was time to turn to the smaller stuff. Photographing and listing pots, pans, and old silverware spelled “major project†to me. And too many phone calls.
Now it was donation time.
You have your choice of charities, all of them eager to take your good stuff and give you a tax receipt for it. We spread the stuff around. Some stuff went into bags and was driven to the local Goodwill store. Eager volunteers, including a one-armed gentleman, came out to the car, grabbed everything and away it went.

Other organizations, like the Salvation Army, had delivery trucks you could schedule online. Put your stuff out on your front porch, stick a label on it, and sometime during the day the truck would arrive and your stuff would disappear. Left behind would be a tax receipt and a big yellow bag so you can fill it for the next pick up.
Interestingly enough, there were some items these organizations would not take. Hangers, for instance. Wire, plastic, wooden, with or without clothes clips – they would just leave them on the porch. And curtain rods. The curtains were OK, but not the rods they hung on.
We went through our closets three different times for charity. Suits, shirts, blouses, skirts, pants, T-shirts – all went to hang (on hangers) on the racks in their stores. The clothing might have been ours, but not the hangers.
Finally, it was what I called “geezer dump time.â€
All those socks waiting years for their mates were thrown out, along with holy and stretched out underwear. Plates that had chips, the Snoopy part of a Snoopy Snow Cone Machine, bunches of small toys with wheels from McDonald’s, faded T-shirts, and worst of all from my point of view – binders of courses I’d written.
At least all this was sorted. Some to the recycle bin and some to the real garbage. The paper from the binders with all my wonderful words went to recycle. My words may die, but the paper it was printed on would live on. The waste company, however, did not want to recycle the binders – too much plastic perhaps.
So after selling, and donating, and dumping we looked around the house and thought, “If only we had gotten rid of all this stuff before, we would have had so much more space in the house.â€

Very true! We too are going through our house. At this rate I just want to donate everything
How true! and I’ve got a bedroom full of stuff that I am going to have to send through the very same process you describe!