The order that actually reduces regret
Documents and anything with sentimental or legal weight first. Then work room by room rather than category by category — a finished room is visible progress, which matters when the total volume feels endless.
What genuinely has a deadline versus what doesn't
Nothing about the physical cleanout has a legal deadline — the insurance and mail items covered elsewhere do, but sorting through belongings can happen at whatever pace the family needs.
When to bring in a professional cleanout service
Volume beyond a few weekends, distance from family, or genuine safety concerns (structural clutter, pests, mould) are reasonable, non-judgmental reasons to get quotes from a vetted local cleanout company rather than treating the pace as a test of the family's effort.
