The answer was surprisingly right in front of my face. PIRATES! With the dearth of recent swashbuckling movies, and everyone's favorite Disney attraction, they had widespread appeal, and their now stylized image no longer carries with it the political weight and negative stigma that the original group of, well, criminals had.
With a theme chosen, I went in search of good models that could be used for beginners painting without being un-fun or lacking too much in detail. While I personally love the sculpts of the fine Swashbucklers range of Wargames Foundry, I could not afford such figures on the tight non-profit budget I was working with. Luckily I stumbled on Old Glory's Pirates range, and was immediately sold when I saw the pictures.
I decided to create my own painting guide to ease instruction, since you can't easily show a 1 inch figure from the front of the room (i have no live video with large screen). I painted a sample figure from our set, using only the limited paint pallet we have for the event, to show step by step how we could work with what we have.
As the even drew closer, the number of attending 6th graders became increasingly uncertain, so we decided to get some extra men to paint. After searching for a plastic option for pirates and finding nothing, we ordered up 2 boxes of Wargames Factory WSS figures. Being soldiers from about the GAoP, we decided they would do. At the very worst, they would work as local island Governors' Guards or the like. The added bonus was that we would have something to practice on before going straight at the nice lead figures.
Given that I only had a rough 2 1/2 hour window for my portion of this event, it was plain that I needed to prep the figures for the kids. So I spent a week filing mold lines off lead, gluing to washers, adding sand to the bases, and priming about 72 models. It was a race to finish on time!