We have had a home computer since 1994 so you can imagine the changes we have been through. I still have my external zip drives somewhere..lol.
Are you saying DVD's last longer than CD's or are you just continually upgrading to keep your data on the newest thing out there?
About 7 years ago, I migrated some 300 3.5" floppies to CD-Rs. It gave me a chance to weed out and decide what I wanted to keep.
Last year I bought a DVD-R. I have some 20 CD-Rs, mostly old software versions. I think about migrating to DVD-R and tossing, but some of the old programs are still usable. I have a laptop that runs Win95 and know people still running Win98. So, I'll wait awhile before dumping the older programs.
Organization is something you have to give serious thought to, as it can be extraordinarily difficult to find one file out of millions if you don't have an easily understandable system.
I figure that as the harware ages, I'll just keep moving it to new higher-capacity hardware. Beyond physical storage, you have to consider format issues. What's the point of having a file if you can't read it. This is why I like ASCII a lot for text. I suspect it will be a standard for some time to come. Once unicode finally pushes it to the dustbins of history, I'll write a script to convert to the established standard. This will be harder with some data types, but I would strongly encourage folks to use non-lossy compression for anything they want to keep long term. i.e., do NOT use jpeg or MP3 for storing pictures and sound files respectively, because you'll lose fidelity during conversion.
This is something people don't think about much because the standard line is that digital copies are "perfect". This is true when making byte-for-byte copies, but if you are expecting to have to someday convert to a new format, you'll regret using lossy compression.