I have a word doc of a wide range "list", ie stuff that I think of for all kinds of trips (diff weather specifically) to help as a reminder to jog my memory of for example, "oh yeah, that fleece neckup would be good to add" sort of thing.

in reality though, each time I do a trip I tend to print out the list and just keep it along with the specific maps or whatever in a cardboard holder or two of various "bike trip/maps/info" stuff. When I think of a trip, I just get this stuff down from a shelf and then start going through things and go over my little notes from previous trips.
I find it handy to make little notes after a trip, like-- didnt use this, too hot, or "wish I had a X" or whatever.

not very organized but I like having it on paper still, to be frank I don't ever see myself doing a setup like you, I'm too much of a lazy bugger to spend the time on it like you have. Guess I just dont have the interest either (computer programs wise) , although the basic idea is the same--keeping track of a "bike list" to not forget stuff and to reflect changes in what you bring depending on conditions and/or over time and wanting to bring less stuff.