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.