eBay if: It is still relatives new and still worth a lot.

If I have the feeling that someone else might find it useful.

Recycling: If it had sensitive data on it and cleaning it up is not worth it at all like small and old hard drives or old and slow USB stick.

Gifting:

If I have the feeling that it would help. Like a laptop which is old but not too old for normal daily use. I will clean it, fix it and search for someone to gift it.

I do try to do something with those things fast as it only makes it less useful longer I wait.

It also annoys you when it is inconvenient like when you move and find all of the old stuff. Or you lost that space for ages and then you throw it out anyway.