I don't disagree with what you say above, but if he's gotten to the point of getting a tax lien against him by the State, and he doesn't know he owes back taxes by that time, he needs to learn to open his mail.
It's not necessarily a big deal, but it's just one of those indicators to me that this guy is no where close to being able to buy (or even run) a business with an income of $250K.
Why? So noone successful has or has ever had a lien on their home?