That must be really tough to deal with, Miemohrs. Lending things out is a good idea, you might find that after it's been out of the house for a while, and you haven't been seeing it around, it's easier to say goodbye to. And if your friend will deal with rehoming the stuff, that's less for you to do.
Yes, decluttering raises all sorts of issues you thought you'd dealt with, as well as some things you didn't even know were issues. Just do things when you can. If you don't feel ready to part with something, leave it and revisit it later. I think I can safely say that most of us have come across items and kept them, only to change our minds and get rid a few weeks later.
I had a rummage in my craft cupboard yesterday and identified a few bits to sell, and a few to throw away. I've been saving some containers, with the intention of cutting a slot in the lid and then decoupage-ing them, to make pretty money boxes. Well, I haven't got around to it yet, and my energy levels are not great at the moment, being 25 wks pg, and having a 21mo toddler running around, so by the time I can actually get any craft done (usually about 9pm) I just haven't got the capacity to get creative. That's not going to change in the next year or so, so I threw them away.
All my decluttering seems to be inside cupboards and hidden areas, so the house looks no different!