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My situation is more complicated than the usual story. I started collecting e-texts over 20 years ago. They would be articles and stories, almost all in plain text. Some of them came from BBS captures. Eventually these included some recognized stories by known authors, such as Mark Twain or Jack London. I started by keeping these files on floppies of the 5.25" variety. I migrated them to 3.5" and had them sorted by topic. This collection kept growing and it was around 2000 that I migrated them to a CD-R.
By 2005 the collection had grown to 3 CD-Rs, and one of them was fiction that was sorted by author's last name. Around that time I had over a dozen CD-Rs with my photos and a few with my art and video content, so I migrated it to an external HD, along with the ebooks.
There are currently two forks of my collection. The "Booknook" fork has fiction that is sorted by author, and "Bookshelf" is nonfiction sorted by topic. This includes manuals for my gear, articles, and a lot of old material that has been out of print for a long time and is scanned to PDF by hobbyists. This means that metadata is not available and would need to be built by hand. I find it easier to drop the file in the proper directory by topic and leave it at that. All of this is mirrored on an external HD, and small portable HD, and two netbooks at different locations. A subset of this library is on 3 different readers and Dropbox. I use Sigil to create ebooks from content, and Calibre to massage formats and sometimes to feed the ereaders. I could see using Calibre to maintain the fiction collection in the future, but not so much with the nonfiction. I would need to develop a conversion and metadata strategy before I do that.
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