My first example came from your text when you said if you asked your mechanic about specialty tires. He is talking about the tires and about how much they should cost; he's not telling you what you can or cannot afford. In my second example, it is a specific statement about how much someone can afford and that's where the judgment comes in. The person saying it has no way to know what someone can or cannot afford unless they have direct access to that person's bank account, so they must be using something else on which to base that assumption. What else can it be but appearance (of the person, of the house, of the car, et cetera)?
I'm trying to explain it a different way for your just in case I'm the one miscommunicating. If you'd rather I not, that's OK, too.
NyaChan - In your first example, I wouldn't see it that way at all because I don't know how long it will hold up. If he explicitly said, "It will actually probably hold up for 50+ years, but in your shoes (as in someone who wants to repair it just in case), you can spend about $1000 to fix it a little now and it will hold up longer." It's without context of what the person means by "your shoes" that turns it into a judgment statement.