Proud Dick - S2-E13
Other mistake: When Dick and Sally are playing with the cat toy in the kitchen, they make a lot of joyous noise while doing so. When the shot changes, we see Mary coming up the stairs to a completely silent home, and she can't seem to locate anyone until Harry pulls her into the closet. The kitchen is only a few feet away from the stairway, so not only should Dick and Sally's voices have still been very audible, but at the very least, Sally should have been in Mary's direct line of sight. (00:15:53 - 00:16:20)
Proud Dick - S2-E13
Revealing mistake: When Harry lands in the yard, you can tell he lands on a crash mat, as the grass beneath him shuffles. (00:01:15)
Answer: The writers often have Dick respond to Mary with a retort that he thinks is in the common vernacular but makes a mistake in wording that is often funny. Dick seems to be imputing a criticism from Mary and responds with a corruption of the more common "I'm going to wear your ass like a hat!" I doubt it has anything to do with owing taxes. Probably just one of the writers assuming a common regional phrase would be universally recognized.
That makes total sense. I always interpreted it as perhaps snowshoes are an expensive item, and given that he was blaming Mary for his newfound financial woes, he was equating her living off his generosity and used snowshoeing as a metaphor.
Phaneron