I'm not sure what happens when we hit a thousand posts on a thread, but this looks like a good place for the new one

I don't know how you can stop feeling guilty about getting rid of stuff. I find it hard too. I read something years ago that said that it is not our job to find the perfect new home for something we no longer need or want. It's enough to recognize that we no longer need it. The object served it's purpose and we do not have to worry about what happens to it in the future.

I also find myself holding onto donation bags/boxes for a long time, long enough so that when I go back to the bag/box, I want to keep half the stuff again. For me, throwing stuff directly into trash or recycling has helped a lot. My trash gets picked up weekly, so I try to go through the house looking for items to toss the night before.

Congrats on getting rid of the bag of clothes, that is a good start!