@speakingtohe Thanks for the detailed response and you've convinced me to give it ago with some of my collection. I think you misread where I wrote it's 250 gb not 25 gb though
@betterred kiwidude plug-ins I'll look into those
@unbogling that is a massive post, bookmarked and I'll dig into it later for sure.
I guess my situation is that I have a large list (48pages) in simplenote of books prioritized by what I want to read next and if it's not high priority it's sorted by subject. From here, I just use "everything" to quickly search that next book on Win or spotlight on Mac, so it hardly matters I have a sorted file system or proprietary software. I know there are times when an author pens under different genres like Iain Banks, but I don't know that use case is gonna come up much for me. I basically know what I want to read and already spend practically no time just going to the next book in my list which I prefer over situation where i'm herding. I know Calibre is far more than this though and curious to see what I can do with it, so I will try it out!
One thing I'd like other than my sequential list is someway to inject some serendipity into what I read next and maybe I can figure out a way to do that with Calibre or a plug-in. Thanks for the opinions so far