We upsized last August but got rid of heaps. 27 years. It was easier to dispose of things closer to the moving date. Early on though tears and indecision. Old house tiny and 90 years old. New house bigger and 9 months old when we move in. Some things don't "fit" in the new property. Luckily most of our furniture did. Regrets for disposing of some things only those that we were ripped of by a dealer posing as a buyer at a garage sale. Modern housing doesn't allow for displaying I.e no mantle pieces etc.
9 months on sorting out some more things to go that don't "fit"
Sewing stuff lots of things given away or sold, miss none of it. Kept patchwork stuff and glad I did. (Husband not so glad lol)
Rattling around nicely in the new house but not liking the suburb much. Quiet means no one is neighbourly (gave up trying after being told we keep to ourselves here) getting use to social activities are all out of area. Both groups I joined "found" me after a fruitless search (who thinks of that when buying out of area where you currently live)