My Gen 3 has been in daily use for just over 4 years now, but for Xmas I treated myself to a new reader - a Kindle Paperwhite. Mainly because 'I could' but I also have been having issues getting stuff onto the Gen 3 over the last few months.
I found that whatever computer I connected to I could see the internal and SD memory, but could never get files to copy to it without an error (the old windows explorer hang whilst writing) and so in the end could only add stuff by putting the SD card into my laptop directly.
This wasn't my main gripe though it was just getting the books I wanted: After Fictionwise I started using Kobo for books, but found the whole, browsing / buying experience painful. Eventually I started buying books from Amazon, but of course still had to go through the process of converting them to mobi (my preferred Gen 3 firmware) that the convenience of the Kindle way of life my partner has became irresistible.
The real kicker though didn't come until I actually started using the Kindle - no twenty second startup that I was used to on the Gen 3, faster page turns, and just whole lot better user experience.
So much as I have loved my Gen 3 it was time to recognize the march of progress and upgrade. What I could do with is a jailbreak for the Gen 3 so I could find some other use for it.