Also, it's saying to get $2 up at the top but I've sold a pick for $5 and it only pushed the bar over a little
Both of your confusions are regarding dollars vs cents. It would be nice if all the units were in dollars, but some of them are in cents. If you're not familiar with cents, they are worth 1/100 of a dollar.
It's the font that's messing with me. I've played a bit more and I think I've kinda got an idea.