We attacked one of the bookshelves last night, as part of my continual drive to get rid of things out of the house and out of our lives. Over the last few weeks we've thrown away 30 or so old VHS tapes we've recorded off the box, and given some commercial ones to charity shops. I've also thrown away a dozen cassette tapes, though must be another 100 to go through. I really don't want to pay the studios again for buying the same music on a different medium (be it CD or MP3), but my options are limited:

transfer from tape to MP3 - all sorts of simple or complex software out there to help me (and if I had a desktop PC some hardware too), but I think the time consumed per tape will be quite high (fiddle with levels, get the track breaks right, title songs right), and I may well not be delighted with the quality of the resulting tracks. I've tried before recording some important items into PCs, and it was always harder than it should have been, and with a loss of high frequencies, and the addition of lots of hiss.
buy replacements through iTunes - dead simple for those albums available on iTunes - but they will almost certainly be locked with DRM, which limits my options unhelpfully. The situation is improving slowly as the Studios appear to be swallowing DRM-free licensing just avoid Apple getting a complete monopoly of supply. In the UK this includes 7digital which is growing quickly.
hunt around on BitTorrent sites for others who have shared the files - after all I have paid once for the song already! However, my limited experience in this in the past for some critical tracks showed it was very hit and miss, time consuming, and of course liable to malware.

It's looking bad. My best bet has to be to take a deep breath and be ruthless about what I really want to listen to still. And pay up for MP3 versions for those that I really want to still be part of my life. Most of the artists I like aren't chart toppers, so they could do with the money ...Now to the books: we got rid of 35 (novels to the WRVS for the hospital library, some to charity shops, and a few in the bin). Unfortunately that still leaves a whopping 710 according to the catalogue :-( We are managing to part with more novels that we've read, so the fraction that are Christian reference books keeps going up. But all of this is less impressive still have calculated that we've bought about 100 books so far this year ... ahem.We've sold a few DVDs off, but we've hardly thought about them, or the CD collection. Maybe I need to ironically buy a copy of It's All Too Much: An Easy Plan for Living a Richer Life with Less Stuff by Peter Walsh to further motivate me to keep the de-cluttering going.