I have been in the downsizing phase as well.
Where does a perpetual traveler (for a while at least) draw the line as to what to keep and what to toss.
And when downsized where is it kept?
In storage? home of friend or family?
I bought into my mom's storage on her property, so no monthly bills for that (she was putting up a storage shed, and I simply paid for part of it). I also reorganized all her stuff and moved all her things out of a storage location for which she was paying $120 per month and now she pays nothing, and it all takes up less space than before with lots of extra room. My mom was happy to store my stuff for free, but I insist on paying her for everything and she does appreciate it. I also help maintain her property when I am around.
If I were paying monthly for storage, I would get rid of more stuff (basically doing the math on replacement vs. storage+convenience). But right now I could fit everything into a 5 foot x 5 foot storage if I needed to (which was my goal). I don't really have that many knick-knacks and almost all my photos are online.
Only on this third phase did I start throwing out things I might actually need in the future. I had some 20 year old dishes and dishware (although family historians assured me they were much older!, ha ha). So I went to the dollar store and looked around and realized that I could get much better replacements for dirt cheap whenever I needed them. I also tried to remember back the last time I cooked for 10 people and served them on my dishes and when paper plates wouldn't have sufficed, hmmm, no events came to mind . . .
So I got rid of that stuff. I also got rid of old books. I had already given a bunch away but decided to sell many of them this summer and got over $1000. I was keeping things like old chemistry and physics textbooks. Then I realized I could get new versions of the same textbook, usually, for just a few dollars on amazon.com used (since only the latest edition textbook is really worth much). Plus, my local library is my almost like my own personally managed collection of books that I can access when I have the need.
Then I started selling other things, like my old digital camera for $85 (which I promptly replaced with a new one for my upcoming trip). I sold a bike rack and an old pair of binoculars, stuff like that. I got rid of more clothes (deciding which clothes to get rid of is very time consuming!). I think I counted 20 sweatshirts, most of which were gifts. How many sweatshirts can I use? So now all my clothes fit in a few drawers and one closet. I actually wear many of the clothes that I own, a first for me. It was painful to even get down to about 15 t-shirts, but how many do I need? And the clothes I wasn't using are being used in a good home. I even sold a small collection of small change foreign currency (like some francs, marks, pounds) that I had from when I was not smart enough to cash in the money before leaving the country!
I still have things like blankets and sheets that I just kept because there is plenty of space for them. Other things I thought smart to keep even though I rarely use them, like a nice 2-man tent, and even tire snow chains (expensive, take up little space). I kept virtually all of my sporting equipment which does not take up much space.
Because of free trade and rising standard of living in the last generation, "stuff" has gotten more easily available and super cheap. The calculus for storing things is fundamentally different than it was a generation ago, when it made more sense to keep things.
Kramer