"Roman Holiday": The Second Sunday puzzle

Last weekend's Second Sunday puzzle in the New York Times is a Mike Shenk creation that was unveiled at last month's National Puzzlers' League convention. There are clues for 25 words or phrases from which all the Roman-numeral letters (M, D, C, L, X, V, I) are removed, with the remaining letters, in order, spelling another word or phrase. The challenge is to figure out what the starting and ending words/phrases are, given the sum of the Roman numerals subtracted in the process.

The example given was:

Deuce, often – 1151 = Military conflict — WILD CARD/WAR (ILDCD = 500x2 + 100 + 50 + 1)

I've got 22 of the answers, but three of them have thus far refused to show themselves to me. Anyone have subtle hints for these?

2. Idleness – 108 = Dapper

3. Motor oil brand – 111 = Steak sauce brand

16. Part of the year during which classes are held – 1150 = Large marble

Wait, I just figured out #16. Still at a loss for #2 and #3, though.