okay...what is Joe-Jacks dream job?

Ranching. Sorry for not putting it in the guide. The only way to win this quest is to sit on it as long as possible until you can unlock and build a ranch.
=)

I worked it out after the third restart of the level. Remember he says he wants to work with rope and the only place he can do that is at a ranch. So do not employ him until you have unlocked the ranch.

I have already lost him cos I couldnt find his dream job, but I didnt get much of a chance to find one for him he left to quickly, does he come back at any point in the game or has he gone for good??