Hello, Pineapple! With art, it's always difficult to say for sure what the artist's intended meaning is. That mystery is one thing that makes art so interesting. Different people can look at a work of art and feel different things or take from it different messages. All of those possible meanings you suggested are plausible and only the artist can say for sure which one it is. "Err" is the verb form of "error". To "err" means to make a mistake, be incorrect, be mistaken, do something wrong. Example: The lady erred by lighting her cigarette in a "no smoking" area.

The beautiful thing about art is that it is subjective to the viewer. What you see and take from art will be different from what your neighbor does. This particular painting is similar to another one he did which just had "Eat" and "Die" on it. This was used as a command, and yet these are basic human instincts. "Eat" in particular was used because it was the last thing his mother said before dying. So while some may see it as inspirational, Eat, Hug, Die, Err, others might see it as morbid and dark. Some might see it as a command, while others see it as simply minimizing life to these four words. This is how I see this particular painting due to the name "American Dream." We fight and struggle and dream of this fantastic life, and yet in the end, life is about eating, hugging, erring, and then we die. But as I said, it's subjective. You aren't ever "wrong" when it comes to art. Err means to make a mistake or sin. There is a common saying "To err is human" and it's said when someone makes a mistake. Because everyone makes mistakes. Just like everyone eats, everyone hugs, and everyone dies.