After importing my brokerage 1099-B, do I need to answer "What type of investment did you sell" question for each trade? I don't recall having to do this last year.

only for the collectibles because they are tax differently but TT in step by step mode may go thru them all.   see if there's a continue icon at the bottom so you can skip the ones that aren't collectibles. 

i believe forms mode is available in premier, so you may want to skip over them and then switch to forms mode to identify the collectible trades.