Can anyone recommend a program or way to tag my images?
Trying to sort out my 1000 or so images from my last trip before I go again in 2 months time. Would love to be able to tag them with things like "Main Street" "BTM" etc etc.
For free, you can use Irfanview (www.irfanview.com), specifically the Irfanview Thumbnails section. It's kind of hard to mix and match tags, but it's easy to add one or two tags to a large number of photos at once.
I also vote for Lightroom. My catalog was a mess until I tagged and sorted everything (all 17k of them). Now I can find any photo I need whenever I want it, and more importantly, my wife can find the pictures she wants as well.