Tricky Dick - S3-E3
Audio problem: In the epilogue when Harry is singing for the garage band, before he takes the guitar and smashes it, you can see the guitar player is strumming, but only the bass guitar and drum parts are audible. (00:21:20)
Scaredy Dick - S3-E5
Continuity mistake: Before the offscreen trick-or-treater starts throwing eggs into Mary's house, you can see she already has egg stains on her jacket from previous takes. (00:17:40)
Character mistake: When Tommy asks Don how he knows his I.D. is fake, Don says it's because he used to date Tommy's sister Sally. Sally, for the purpose of the aliens' mission to study Earth, is supposed to be Tommy's aunt. (00:14:25)
36! 24! 36! Dick! (1) - S3-E14
Revealing mistake: The mandolin that Dick is playing has no strings. (00:15:40)
Dick and the Other Guy (2) - S3-E23
Audio problem: When Liam is performing karaoke at the end of the episode, his mouth is not even moving for some of the lyrics, and there aren't any vocal tracks on the song, because only the instruments are heard when he abruptly stops singing to admonish the crowd for trying to leave during his performance.
Sally and Don's First Kiss - S3-E24
Factual error: When Dick is purchasing his lunch, the cashier tells him the total is $3.75 and he incredulously lays down another coin because he thought his total was going to be $3.50. When he walks away with his tray, you can see that he paid for the meal with 4 coins. Unless he paid with silver dollars (the Sacajawea dollar had not been minted yet) then there is no way he could have covered the $3.75 with just 4 coins. And if he did pay with silver dollars then it would have been completely out of character for him to not have gotten any change, seeing how the show has established him as a cheapskate, as well as he would definitely get change seeing as how upset he was at having to pay an additional 25 cents for his meal.
Revealing mistake: When Harry throws the tent against the ground, his left foot bumps against the large rock on the ground and the rock moves. (00:07:20)
Revealing mistake: Near the end when Randy is driving away with Harry you can see that the steering wheel doesn't move when Randy turns it.
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