The question of what might you need in the future is one that gets me to dump things quicker. There are many things I haven't used in a long time and don't anticipate using any time soon. Some of those things I won't ever use again. For instance I have motorcycle saddle bags and no motorcycle. I found them useful for carrying my dog on bicycle rides. I don't do that now.

Those are easy choices. When I sold my parents jewelry and some of mine (class rings, an expensive gold pendant) there were plenty of memories attached to those items. There was no lack of sentimentality there. Those items were purchased and honestly they weren't very unique. They were just sitting around in a jewelry box. I might look at them once every couple of years.

Personally created items, things made by relatives, unique artwork, and such might be difficult to give up. Unless you absolutely need the space or can't carry them in your new lifestyle of living out of a bicycle trailer, why get rid of them?

If you keep things as investments then they should be kept until it is time to cash in.

Everything has a dollar value. With personal or sentimental items you might find the dollars are more useful to you than the sentimentality.

With today's great technology we can photograph and make digital videos of everything. That can help you maintain your memories without the actual item being in your hands. An external hard drive or even an online storage site can hold thousands of your images and movies for a tiny bit of money. Your feelings and memories come from within you. The physical things just help trigger them. Photographs and videos would probably be just as good at triggering them.

I've sold items for less than they would be worth if the right buyer came along. I didn't want to wait around for an indeterminable time for the right buyer so the items were sold. A bird in the hand is worth two in the bush.