I guess I have had good luck landing what I wanted in terms of free travel and upgrades.
However, I can be usually flexible a few days around my desired dates. For example, just today, I booked two K-class tickets with BF upgrades BOS-NRT-BOS. I paid $990+taxes for each. My first choice of dates was not available, but I gave the agent discretion on a 4 day window around my first choice, and he was able to land me what I wanted.
Now, this might not be a big deal in low or shoulder season, but these are for early-mid June in the middle of the World Cup (which I'm going to see

). To be fair, I was dreading the phone call to the elite desk: I was expecting the usual teeth-pulling experience of finding routings and rates that at least weren't painful to think about. I was quite surprised at the ease of the transaction....