Most of my readers now have fewer than 100 books on them after I ran into some problems and had to reset to the factory settings twice. Rather painful, but it fixed it. So, rather than reloading all of them, I just limit to current stuff. Like Harry, I like to keep a series together, but I keep the entire series on the reader. When I have finished a book, it goes into COMPLETED in case I need to refer to it while reading a later book. I currently have 2 series on my take-a-long kindle - one is a mystery series and the other science fiction, so I can have a choice.
Now, my choice might be different if I didn't have easy access to a computer at most times. It was kindof a pain when I was caring for a family member away from home and could only update my ipods/readers once every 3 weeks or so. I was just used to instant gratification - it really wasn't a big deal except for library books that invariably became available at times I had no wifi access (no smart phone here). I plan better now that I've had the experience. I also have multiple readers.