i've done a LOT of uncluttering over the years, got rid of thousends of items. Its an on going thing espcially with 3 growing kids. it's never "done".
I can honestly say in all this time, that even the items that were harder to let go of have i never regretted letting go of anything. (i take photos of things for memories)
I wouldnt get a skip though unels syou ahev piles of old plasterboard and carpets laying around, best to try and get rid of things reposibily, freecyle, facebook market place etc, charity shops, car boot sale, ebay, friends and family etc and then only recyle or throw out stuff that really has no value to anyone really (holy tshirts, school work books from 20 years ago)
I'm not totally unsentimal though we each have large 2 palstic storage containers we can store memory stuff in and limit it to those, if we want to add stuff and its already full something has to come out to keep a limit on it.
Everyone's "enough" is diffrent though, if what you are unsure of dissapeared tomorrow - would you notice? what you go out and try to buy the exact thing again to reaplace it? if not its a no.