Rook, it looks like you have put a lot of thought into this.
My experience with insurance has been sometimes it pays off and sometimes it doesn't.
With perfect 20/20 hindsight I could have fully insured my new V4 Ducati but in this case, without a road hazard addition to my policy, my insurance wouldn't have paid it anyway.
When you purchase full coverage insurance, you're betting you will have a problem, the insurer is betting you won't and in the long run they typically win.
I've alway heard to insure only against catastrophic loss like your house burns down and self-insure for everything else.
On bikes, it only makes sense to fully cover for a few years until the bike depreciates and then drop to liability only.
My VTX1300C is 21 years old and worth maybe $3000, it gets liability only, if I wad it up, it gets sold off as parts or salvage.
At the end of the day, none of us can predict when we are going to have an accident, if we could, they wouldn't be called accidents.
This thing with my brand new V4 was a freak, a million to 1 but I choose to look at the good side, it could have been so much worse if I had gone down, hit a guardrail or another vehicle head on when I lost the back end.
2021 Aprilia RSV4
2020 BMW S1000RR
2016 ZX-10R KRT
2016 959 Panigale Red
2015 CBR1000RR SP Repsol
2011 ZX-10R Ebony
2009 ZX-6R Lime Green
2006 ZX-14 Red
2004 VTX 1300C Candy Red
"For we walk by faith and not by sight" II Corinthians 5:7