I think the risk/reward was pretty close. I went through what DC has to do in the Running the Numbers thread last week. Going into last night's game, DC had 3 Away games left against NYCFC, RB, and Chicago. If you assume 3 points there, they probably needed 23 points in their 12 home games. Those include games against Portland, Atlanta, Red Bulls, Dallas, Toronto, and NYCFC. They probably need to be near perfect on the other 6, including Orlando last night, to make it.
I doubt it was a smart move strictly by the odds differential, but Olsen knows he has little room to drop points at home against bad teams. It paid off in the most backwards way possible