Yes it means it's a difficult task, path to take, course of action, etc. It's not a common expression (I've never heard it). A much more common expression that means the same thing is: It's a tough row to hoe. It's funny that this is still fairly common - it is derived from farming, which doesn't involve that many people nowadays.

Yes. Will depend a little on context, but surfing is survival, mastery, playing happily, so could be taken to mean any of these, I guess. .