So, keep in mind, one's man's trash is another's treasure.
Quite true, have very ambivalent feelings on the topic; As briefly as I can.

I am a terrible hoarder / collector, see value in everything. Got the tendency from my parents, both of whom are thankfully still alive, but realistic about what the future holds. What is to be done with all of the "junk" is a topic of discussion, something we worry about, but when push comes to shove they are not ready to let go of anything, regularly make room for
more. And it's good stuff all, junk is in "air quotes".
Then recently and suddenly, the problem wasn't what to do about all of their stuff, it was what should be done about mine. Health issues, lost my job, lost my direction, lost my home....bad situation. The kind of bad situation where there simply isn't time to make intelligent decisions, only frantic, desperate ones.
Patticake, if at all possible, I would say earlier suggestion of PODS or similar, a good one. Give yourself some room to let the dust settle; Once the stuff is gone, its gone.
None of my stuff was great stuff, with high street value, (that 'aint me babe) but the number of trips I made to the dump, and threw into the pit, stuff that should have found a new home, is crazy. Old tube radios, vintage Italian car and motorcycle parts, antique adding machines, machine shop tools.....on and on.
Once one makes the initial, ruthless cut, the natural sense is "what remains is the stuff that survived the cut...it must be valuable, can't be gotten rid of, so I never will" In truth, having made that first cut, it becomes increasingly easy to carelessly chuck stuff you might regret later.
On the other hand, it is just stuff. In the moment, I told myself " I have bigger fish to fry, not my responsibility to organize the world". While I do not feel "lighter" or "free" without all that stuff, (as others have suggested I would), neither was losing it the end of the world. Particularly when it comes to personal items, family items with high sentimental, but low "street" value: 1) Hold the item in your hand. 2) Have the memory. 3) Having had that memory, accept that the item has now performed its primary function. Maybe keep it, but don't beat yourself up too much if you can't. 4) Repeat. Easily said, hard to do.
While I was not able to save many things, I was able to find a good home for many others.
My grandfather was unimaginably important to me; Lived a wonderful life, had many skills, among them an outstanding furniture/cabinet maker. Had two daughters, my Aunt got the silver in the will, my mother got the power tools. We laugh about it to this day, but illustrates how important the tools were to him. The Black and Decker power saw that he bought new in 1960, found its way to me; Solid aluminium, no plastic or safety features, complete with the original receipt, operator's manual, and warranty information filled out in his unmistakable hand writing. I built significant parts of my house with it, but the day came when I had to let it go. Put it on Craigslist. First person to respond very interested, we did a little back and forth. I made some assumptions, and the buyer's name gave me no clues, so when all 98 pounds of her showed up, (forgive me) all I could think was "Honey.....this might not be the saw for you". I gave her the (uncharacteristically short

) version of the story, she handed me the $40, and walked down my gravel driveway, one arm stretched out way longer than the other, saw in tow. She got all the way to the street, turned around, and lugged it all the way back. "I wanna' know" she said, "It's important to me.... What was your grandfather's name?". It was really sweet.
One way or the other, you will get through it, one way or the other you will do the right thing.