The older you get, the harder it is to save any papers. At 61, I have moved dozens of times, and it’s just too much to schlep around. I regret that I’ve lost letters — some from famous dead authors, some from college friends sending me their impressions of Europe in 1971 — and my own manuscripts (I won first prize in a playwriting contest as an underground and “lost” that ms. maybe 30 years ago). The only thing I keep are my bound diaries for every year dating back to 1969, and I’ve been trying to digitize at least a fraction of the 9-million-plus words because I know they will be lost too, stored for many years at the house of relatives.
Now it would make sense to scan and save your most valuable “papers” as a file, but who knows how long it will be before the file is obsolete? I wrote stories and newspaper columns that were saved in some long-abandoned format when I had computers like the TRS-80 or word processing programs like PerfectWrite (IBM). All I have left of them are scanned JPG files of the photocopy of the published pieces.
You should keep what you think you’ll want for a few years out, but eventually, hopefully, you will get older and older and it will become more of a problem to keep the accumulating “papers.”
Perhaps one’s G-mail chats last forever, though. Sigh.
I get rid of almost everything. On multiple occasions, I’ve thrown away/deleted everything I’d written over the span of a year or more (I don’t do this anymore). For a similar reason, I’ve only kept two of the print publications I’ve appeared in, and only have a copy of one of my books (though not the English edition, so I can’t read it).