Obviously, you don't want to get in a habit of overpaying in trades. Also, obvious is that we are playing better than ok and the sky is not falling. That said...
The future as far at it pertains to getting a star looks very bleak. a few months out from the deadline and there are no real rumors of a disgruntled star. There do not look to be a lot of star FAs to get in the summer and for the next 2 summers everyone will have max money to spend. Maybe we can get some draft luck for a change, but any rookie we get will probably not help us tremendously right away. So for all these reasons, it may be time to make offers we wouldn't otherwise make.
I've said it before, but I really like what we have in AB, Smart, IT and Crowder. The preference would be to trade even the nets picks before trading them. So if we can keep them, we don't really need help at the 1 and 2. If we can get a really good 3, we can move Crowder to the 4.
So guys that fit the bill for our need, guys that haven't been rumored to be on the block but seem like they could be traded are guys like DMC, Melo, Howard, Durrant exc. It might make sense to over pay to get one of them. Think of the opportunity cost. If we can make ourselves a top 5 or 6 team this year, we can probably get a FA this summer that we otherwise could not. The same is probably true for next summer.
If Ainge started calling around offering Lee and other players plus ALL the picks, would teams like Sac, NYK, Hou and OKC have any interest?