I think things are a lot more standardised these days. More and more software makes it easy to take PDFs of documents, some automatically save them as PDFs. Lots of different bespoke software packages use proprietary database software behind the scenes. That means that even without the "front end" being available in years to come, the data behind it could probably be read by using the proprietary software. But, I think we're talking more about "documents" here when taking about comparing agianst physical photos and diaries, so we're not really looking at long lists of 0s and 1s, we're looking at the format in which documents/photos have been saved, which is usually pdf and jpeg.
When you go back 30-40-50 years, a lot of software developers would write their own code from the ground up, even their own operating systems, but over the decades, there's been a lot of standardisation. Most systems these days (particularly domestic and small business ones) seem to provide for data import/export so there must be common file types baked in, even if it's just as a simple csv for data.
For example, I had hundreds/thousands of holiday photos uploaded to the truprint app. I never felt secure about them being stored by a third party in the cloud and was relieved to see that it was relatively easy to download them as JPEGS in zip files, which I did and have now unzipped them and downloaded them onto a portable hard drive and uploaded to the cloud in the form of dropbox, so now have them in three different places (in fact, four because I have them on my laptop too!). My family know my password, so hopefully if anyone is bothered, they could find them after my demise. Obviously, if they don't, then future grandchildren etc won't find them either. But that's the same as if my next of kin just chucked all the photo albums in the skip when clearing our house when we've gone!
I think the answer has to be for people to be more aware of where they store their documents, how they're backed up, making sure their family know where they're stored with passwords, etc. A kind of "will" for the world of modern data.