Bidding Strategy help-

Going through training on the 7ERB NYC, was told to shadow bid. I watched the Youtube video and read the gouge, but there really is not much there. I understand it pays the higher of what I can hold or OE trips. Question is, I finish training the first week of November, should I try and bid trips and reserve in the first couple of weeks of Nov. and try and bid days off towards the end? Any help would be appreciated.