Given his own background, the idea that he'd raised a daughter who clearly seems to have never realized that she was supposed to have a plan in place if an unplanned pregnancy, unexpected job loss, disability, illness or catastrophe were to disrupt a life in which nothing was ever supposed to go wrong would, at the very least, annoy him. I mean, imagine that you're him six years ago trying to explain to Deanna that she and Michael should have had a conversation about what might happen if their apartment was destroyed and put a plan in place and realizing that she was too smug and stupid to see the glaring flaw in Mike's plan to run to Mommy and Daddy and let them fix it. You probably wouldn't be too thrilled with her or your son-in-law if you were him.
The problem that faces Wilf is the same one that faces all of us: trying to decide which improvident nitwit to be more enraged by. My guess is that the annoying would-be artiste who's too freaking big and important to watch sports with him would be the less irritating fool. Sure, he might be as dumb and immature a sucker as Deanna but he is on the level when he says that being a kept man is truly the best thing he could do for his family; he might be a dumb-ass but he's a sincere twit. Deanna is a different story all together though; it's always irritated me that the same person who bleated about a domineering mother and weak father playing politics has no idea that she's describing herself. Ah, well. At least her lack of awareness is a consistent thing; she has no idea that what looks like family politics was actually Mira trying to make her tomorrow better.
Nor, I should think, would she be able to make sense of any remark that has as its basis the very real concern that at some point, the gravy train might somehow derail. Trying to explain to them that it's entirely possible that Gordon might go under would elicit the same reaction that John's telling Elly about comprehensive life insurance had: bawling piteously and wailing about being scared.