Um. I live in that town. I have $120. Those of you that think this is cool:
Hard to describe why someone thinks a certain item is cool. I just think they are neat. I like drop front boxes. I think the badge style is cool. I like the drawer layout, good size. IDK. Personal taste.
2. What does it take to strip it and repaint it? I don't "do" details or "fine" work very well.
I would NOT, repaint those boxes, especially since it sounds like you will do a half a$$ job. They look to be in very serviceable condition as is. Repainting a box with a good job is a VERY time and skill consuming task. Majority of the time, when people repaint boxes they turn out worse and less valuable than when before. Note, I said, majority, not all the time.
BTW, welcome to GJ

If you do purchase them, please post up some pics.