Packing

Packing, not my favorite thing to do. I'm finding it's difficult to throw things out, especially things that have a sentimental value to them, but that I don't use or want or need.
For example: a gift, that is difficult, what do I do with something a friend gave me that I'll never wear or want to decorate my home with? Do I keep these items because I'd feel bad otherwise, and why. Does the person who gave them to me even remember. And it's not like you keep everything people give you the rest of your life! there's got to be some kind of protocol to follow. I guess it comes down to how much I care what someone thinks... I mean if the person did find out I threw something out, or gave it away, would it really matter? Why does it make me feel bad. And am I the only one who goes through this predicament?
Also finding it difficult to part with something like an old journal. Old memories. I want to be able to just throw things away without feeling guilty or regret. What is that?
I guess as I pack I realize how much I have that just takes up space and I how much I don't want clutter in my living space. I also just want to simplify. It's much easier to have less choices. So my thought is to get rid of excess. But I run into these walls that keep me from getting rid of things that were a gift, handmade from someone I love, have memories or value from my past (Such as the paint box I used in art school to hold my oil paints. It's filled with old paints, and brought back memories to hold and look at. But it's not functional, and would be easiest to just throw away, which I want to do, and which spurred this blog post).
There seems to be this conflict between function/simplicity/nostalgia. As I'm packing I'm focused more on Function of items, is this something I need and use. But as one lives in a place and people enter one's life, often gifts are exchanged, and memories shared. Journals are written. Life happens. You're not thinking (or at least I'm not) about packing up and cleaning out. But perhaps I need some sort of routine, that includes this sort of thing, twice a year. Something like spring and winter cleaning. I suppose the other issue is finance. If I had money to afford to spend on replacing all the old with new, it would be easier to part with items. But because I don't I feel like, "well, it's better than nothing". Like some of the furniture I have I picked up for free off the side of a road with a friend. It's functional, but definitely not how I want to continue decorating in the future. None of my furniture matches!!! All are different kinds/shades/paints of wood. Eww. But, I can't afford to replace it all right now, so I say it serves it's purpose. I guess I could paint it all myself. Maybe I'll do that. Stain all the wood one shade/color. Hmmm...
Okay, I think I've procrastinated enough ranting about my issues with organizing and packing. Thoughts?