I've had a similar problem as I've been in the process of clearing and sorting clutter for years since moving in to look after my elderly mother and some of the things have been hard for me to get rid of.
What has helped make it easier is taking photos of items of clothing so there is still a record of it but the item can then be released to charity.
I look online to see if a favourite vhs video is available on a cd which would take up less space and allow me to get rid of lots of those videos.
I put things into cardboard boxes over several weeks and make it a rule never to delve back in or I might have second thoughts. Then I phone a charity who come and collect the boxes. They will come in and carry heavy items downstairs so I don't have to do a lot of hauling about.
I also get onto Freecycle to advertise larger items as then the recipient will arrange the right size transport to take the item away for free.
A lot of it is psychological and the thought of just putting something special into a dustbin feels wrong so my way round that is to put the item into a bag and tie that and then put that into the bin.
Another thing which might help is to think about how much someone else, a collector maybe, would love those items.
At the start I would walk into a room, see all the stuff and walk out in despair, not knowing where to start but doing a bit at a time really ends up making a difference.
What else has motivated me is watching those tv programmes about hoarders as I didn't want to be thought of like that also when I checked online for a clutter clearing service and saw the price they charge I just had to get stuck into it myself.
Anything that I think might be worth money I put in an old suitcase on top of a wardrobe but those aren't large items.
I always wanted to clear the clutter but found emotional hurdles with some of the things I came across so I understand both perspectives on your problem.
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