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Notes -
So far in the history of electronics/computing, I feel like there have been few actual dead ends on the question of transferrability, particularly when the stored data is already digital (and my sense is that probably a majority of analog data resulted in at least one device capable of conversion to digital, even if it wasn't widely used). So, I think I'd be less worried about whether we can get your digital file off of your 2020s hard drive and onto whatever storage medium people will be using in 2120.
File interpretability seems like potentially a more difficult challenge. Look at all the old, like, DOS software that is becoming harder and harder to use. Sure, DOS emulation exists now, built to run in Windows, but if we jump to a new class of OS, who is going to write the new DOS emulator? Or are we going to end up with chains of "new OS emulates Windows, where we have a DOS emulator"? This would seem incredibly brittle and unlikely to be well-maintained enough to not inevitably have some significant number of original files become unsupportable.
That said, when it comes to digital books in particular rather than executables and other files generally, I wonder if I can reel us back a bit. If I fire up Calibre and look to convert a book, I see 18 options. Not all of them are really relevant, but there are a bunch. So I think the numbers game works in a different direction than that of the DOS example. The trend for executables seems to be toward not many different OSs, so if at any point, one backwards chain doesn't get emulated, you lose everything prior that was dependent on that chain. For pure data storage formats, if I can freely and easily replicate the same data in 10 different formats, all I need is one to make it into the new OS, and I've still succeeded. Hopefully, the same numbers game will happen in the new OS, and that one surviving format will become convertible into whatever ten new formats come along with the new OS. That the other nine died is immaterial in this case.
So, perhaps the strategy is that we just need to have people like you continuing to fill their hard drives, but make sure you don't collapse everything down to a single format. Have a script in Calibre or something that automatically converts every book into every format and store all of them simultaneously. Storage is cheap, especially with file sizes for books being so small.
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