I'm normally not the kind of person who thinks the Blazers should be making trades.  I think continuity is undervalued in the NBA and that it's usually better, all things being equal, to allow your young guys to grow and develop within your system than constantly try to find an external fix.  I also should stress that I don't think the Blazers *need* to make a trade. I'm not at all panicked by the way they've started the season.

That said, I think a fairly compelling case can be made that the Blazers should be actively exploring trade options early in the season.  Maybe not right now, but at least as soon as Dec. 15 passes and recently signed free agents become eligible for trades.  Here's why:

• The Blazers have two major rotation players (Travis Outlaw and Steve Blake) who have expiring contracts.  It is highly unlikely that the Blazers will re-sign both of these players at season's end.  Blake may be re-signed, depending on the circumstances, but Outlaw almost surely will not be.  If we don't sign them (or trade them by the trading deadline), we will get no value for them. 
• Outlaw in particular may have more trade value right now than he will at any point in the season.  He's playing extremely well.  If he goes into a slump (which he's prone to do), his value will diminish.
• McMillan clearly doesn't know what to do with Blake at the moment.  He doesn't seem to have the heart to move him to the bench, but he also needs Miller to play the point.  The result is a bizarre lineup where Blake plays shooting guard for much of the game, a role he's not really suited for--offensively or defensively. 
• Having Blake play off-guard takes minutes away from Rudy Fernandez, who is starting to give off the early signs of being disgruntled.  Moving Blake may be necessary if we wish to keep both Miller and Fernandez (which I think we should).
• We also have another promising guard who deserves playing time (Jerryd Bayless).  Moving Blake would free up time for Bayless to get regular minutes.  I realize this is a recurring debate here, but for the record, I think Bayless will be a quality combo guard in the NBA.  He just needs regular playing time to get comfortable out there. Sometimes you have to take a risk on a player. Giving Bayless the 4th most guard minutes on the team is a relatively small risk in the grand scheme of things. 
• It is unlikely that McMillan can keep Blake in the starting lineup for long, but as long as he's there, his trade value will be higher.  If he's relegated to a bench role (which seems inevitable), his trade value may decline.
• If we're going to make a trade at some point (and the contract situation strongly suggests we will), it is better to make the trade sooner than later.  Whenever new players arrive, there is an adjustment period.  It is better to get that adjustment period over now than shakeup the team's rotation later in the season.  If you make the trade now, the new guys will be well-integrated into the system by playoff time.

So to sum up, it is very likely that Outlaw and/or Blake will be traded (or at least seriously shopped) at some point this season.  The trade value for both players (at least as players--not contracts) is unlikely to ever be as high as it is right now.  So if we're going to trade them later, why not trade them now and give the team more time to adjust to whatever the new rotation will be?  Now obviously I don't think KP should pull the trigger on just any trade.  If he doesn't think he can get anyone of real value, then there's no point making the trade.  Also, if there's reason to believe that Outlaw and Blake's expiring contracts will be of significantly more value near the trading deadline than now (so much so that it makes up for their loss in trade value as players), then it might be worth waiting.  If I were KP, though, I'd be putting feelers out there right now and seeing what I might potentially be able to get (either now or after Dec. 15) in exchange for Outlaw and Blake.