Hello @coquicoin, I totally get what your husband expresses about the "what if's". I think it's a smart question, and sometimes you just have to bite the bullet and do it. It's takes a lot of courage so don't be too hard on yourself.
I think it became easier for me because I was always uprooting to go live in different countries.
When you start to travel possessions weight you down more and become obstacles; That forces you to make practical decisions.
Scaling down to this size was not easy, but maybe you could start with a little at a time.
Set yourself goals: maybe test few items to see if you use them for 6 months, and then after 6 months, move them to another location (like an archive, so to speak), and then if not used for a year, then find someone dear to you to give the item to.
Thank you for your nice feedback:)
I think one day you'll find the entire thing easier.