I think we can safely view the 1980s/1990s as the testing grounds for finding out what works and what doesn't.
Naturally, the things that worked were acquired and consolidated by larger and larger companies, which allowed tech to be cheap and commonplace.
The #1 necessary factor for something being accessible later on is the sheer amount of popularity it enjoyed in the past.
E.g. I think some common interfaces, like SATA / USB Type-A will never die, willing to take a $10k long bet that they will still be easily accessible in 15-20 years. Maybe not as popular as some newer ones like M.2 or USB-C.
> Lots of files from the last two decades are inaccessible to me
Yes, but not by volume. The amount of files ever stored on all 3.5 floppies in the world could very easily fit into a single server rack these days.
Are these 0.01% of files more valuable in proportion than others? If not, then it makes 0 sense to focus on preserving those interfaces.