I sorted stuff by ages and, very roughly, by content ages ago. So it's not horrible. By biggest issue is that when I first started using Lightroom I didn't really have a good orderly ingestion workflow so there's a duplication of raw scans, PSDs, JPGs, different versions of edits, etc. It's hard to automate and what to save and what to toss from the catalog is somewhat a matter of judgement.

>I ran all my family photos through a script that renamed them based on the year, month, and date.

I actually don't care about the filename, although maybe once things are cleaned up I'll do an export of everything. It's all in a Lightroom catalog now. It's "just" a matter of adding more primarily location-based metadata and making sure everything I especially care about is in appropriate Collections.

Years ago when Flickr made a big change and I needed to extract my original uploaded content (almost same exact scenario as this thread), I found this script as a starting point (it uses jhead): http://neverfear.org/blog/view/148/Rename_all_jpeg_files_by_...

For me, Flickr has always just been about copies of local files. At some point though, I do need to look at what all I've uploaded there. At one point, my Lightroom database got corrupted. I was able to recover it but I lost the local service mirror of what I had uploaded. (And a fair bit of stuff pre-dated using Flickr in any case.)