harder? maybe.
maybe not.
you can play pretty much all, even very obscure, arcade games with information taken from them being ran in your modern computer. in the long term, things tend to work out for this stuff. once you can easily train some algos to run emulation of old sw and "manually" move over data you wont even be having trouble with spreadsheets, databases in crazy formats or any of that. I'd worry more about the short term readability and preservation.. like, currently I can't run most of programs I wrote for living only ten years ago on anything buyable from the shop today(as brand new items). which could have been said for the amiga circa 1996 I guess - now getting amiga stuff written in say 1990 in almost perfect quality on modern pc's is pretty easy.
(so, maybe someone writes a series60 emulator in the next 10 years - the so called emulator that was used for developing was actually a win32 shim.. so it was useless for developing, since it involved a different memory model and compilers, haha. there wer some rumors of some true real arm emulator research projects though.. ).
and i someone finds digital stuff from today 100 years from now, they might find it interesting. howerver if they find a memory card from today 5 years from now it's worthless, the same card 10 years from now is a curiosity, like the 32mb sd card I keep around, and the same card in 50 years is a rarity and in 100 years an artifact..