I'm earlier along on the "getting rid of stuff" journey.
My first major eye opener was when I realized that my "stuff" was fast becoming the only obstacle preventing me from fleeing an abusive dynamic. I began throwing things away, sneaking out loads to donate and other loads to a 5'X5' storage unit, leaving behind only items I strongly preferred to keep but wouldn't terribly mind if something 'happened' to them (an odd category, to be sure, but one I felt I needed for that time).
Once I got established in my van, I downsized to a 3'X5' and naturally became less choosey about where "stuff" went. That leather jacket with loads of sentimentality to me that I wanted to personally give to some cold homeless person...or at least to a drop-in center where I got some clothes myself for free...eventually found its way into a random clothing donation collection bin on the side of the road. That took a lot of emotional checks to make certain that I really wanted to do it. I simply didn't have room for it. I still feel emotion when I think about it, but not an ounce of regret. It was the right decision, I had - and have - higher priorities and it was cluttering up my life and my mind.
Many things I used to save for donating, I now just toss. Many things I used to save to sell, I now donate. It's like the opposite of "leveling up" in that my riddance of stuff "levels downwards" by letting go of it more freely, more quickly.
I honestly find that for myself this is a really organic process, and others' minimalist "rules" tend to strike me as too harsh for me personally, at least right now. 'Maybe' piles do get easier for me over time. "Why the hell was I hanging onto this??" can and does come up when I'm sorting through maybe bins. Or "Hey I've been looking all over for that" also happens. When an item begins to drive me crazy from remaining in perpetual "maybe-land" then I begin throwing various techniques at it until the matter is settled in my mind, through logical reasoning to sentimental empathy to psycho-analyzing myself to figure out why I'm having problems with this at all.
I do find it becomes easier over time, and the stuff whittles down smaller all the time and I gain momentum as I go. But being minimalist was never my goal. I simply wanted life to work, and for me too much stuff very quickly impedes that. Many of my dreams in life involve lots of "stuff", and I'm not ashamed of that. But life isn't in the stuff, it's inside of US, and whenever that life is getting suffocated it's time to do some pruning order to breathe free.
I don't know if I'll ever give up my storage unit, if I do I'm sure it will be when the time is right for me to do so. I'm comfortable with my "stuff quota" expanding in whichever direction happens to benefit my life at the time, but in the forseeable future all I see is wanting to shrink my "stuff footprint" down much smaller.