AO, until; a few years ago I would have agreed with you about filenames and managed directories being king. I would also not have trusted software to sort them.
Times change, and file systems have come a long way. I regularly use Picasa, which can see all of this info, but does nothing with it, and music filing software that sees it and uses it impeccably. I trust that, and was fairly sure that there would be something that would do the same with images.
I'm actually doing this for the kids really, bit of a health scre prompted it. Hosted online storage doesn't work for me because a) it's moderately expensive for the amount of data I have (although this will reduce a lot after I've sorted the problem this thread addresses, and b) it's not permanent. If I stop paying it would disappear. Who knows whether the kids would want to pick up the tab. After this sort out, everything will be going onto our own 'cloud' hosted on a server here.