Watching the first half I thought the second half winner's circle was significantly more brutal than that in round one and indeed any episode thus far. Re: the $3,000 box, how many other answers were there?
The $3,000 box was a category where you were either going to be able to make the connection quickly or having a million years wouldn't help. In terms of other clues, "poodle", "christmas tree," and "Catholic schoolgirl's plaid uniform" came to mind.
$4,000 would have been gettable if the clue-giver had been able to stay calm. Al was almost there, but he only ever got a couple mediocre clues and some nodding.
$5,000 was not impossible, but if you don't get it from the figurative meaning the clue-giver used, I don't think it's possible to circle around and try the literal meaning. There is one clue I can think of that points directly to the word, but it requires knowledge of a relatively recent Broadway musical, which might or might not work.