I'd have to know what the protection on that pick is before I'd definitely say yes or no - but Jared Dudley is a pretty good defender. Is he a lock down defender? No, but we're sure Iman will be in a position to be this year? Dudley makes Melo playing the 4 easier, and would fit in seamlessly on offense when Felton and Chandler have the PNR game rolling.
To play devil's advocate, I think of it like this - if he's absolutely vital to have on the floor in a series vs Chicago - it comes at an expense elsewhere. We're all in agreement that JR is this teams best SG, right? So, to get Iman on the floor, I think you have to go either Felton/Iman/JR/Melo/Chandler OR Felton/Iman/Melo/Amare/Chandler. The first lineup is too small to play Chicago, will get murdered on the boards + on the block. 2nd lineup, Bulls are elite defensively and defending PNR, and you're asking Iman to be the guy spacing the floor. This takes away what we've been great and forcing things back to isolation with Melo IMO. If we are committed to the 'Big 3' playing together, I just do not see it happening with Iman. Personally, I'd let Felton and JR take their chances with Rose and let him shoot 25 times off surgery. I don't even think playing smaller vs Chicago is possible but if were to be, Dudley/Melo pairing at 3/4 gives you a slightly better chance.
Necessary match-up #2 seems to be Miami:
You can go small here with either the 2 PG's + Iman or PG +Iman/JR at 2/3. The problem is, you're asking Carmelo to guard LeBron. As this roster stands right now, we have nobody outside of Carmelo that can guard him. There's no insurance if LeBron picks up quick fouls on him other than sending JR to the slaughter like last year. This is a match-up where I think Dudley helps. He fits in terrifically as a spot up shooter off of PNR (his best asset on offense) and is someone who can give Melo a breather and wear on LeBron, or try to. If you go with the 'Big 3' together in this series, it's the same problem...how can you justify Iman over JR on the offensive end? Again, I'll take my chances with JR defending. And on the Carmelo being the only guy matching up with LeBron thing - if you're goal is to really win a title, if we somehow get out of the East - there's more than likely another once-in-a-generation SF waiting for us.
Other match-ups - Rondo is gone (Dudley as extra defender vs Pierce would be nice(r) - back court defense is needed for who? Bradley? Lee? Terry?). Brooklyn - They stink. Atlanta - they stink. Milwaukee- sure, I see Iman's value in that series, but if we can't beat them it's not meant to be. Indiana - you almost have to play big like vs Chi. JR is better option at SG.
I like Iman, he has a bright future but I lean to taking that trade MOSTLY because this teams window is pretty small - and there is a chance Shumpert just isn't ready for the role of 'stopper' this season and can't find himself on the floor that much. I think Dudley is at least as good of a player right now and adds value on offense with how this team operates when they're moving the ball and working off of Felton/Chandler. It's also not sacrificing a ton defensively when you take into account LeBron and Paul Pierce. JR is better, and even with Kidd slowing down lately the 2 PG lineup has been this team's best lineup (next to a small sample size of Felton/JR/Big 3). I've just thought for a while Iman is an odd-man out this year and relegated to 15-20 minutes when it counts.
Why I would say no - have to be sure we can re-sign JR this summer. If not, then I wouldn't do it because there's not much left of Kidd and it'd make the back court of awfully thin. Don't need to add an extra SF for long-term. And if the pick is protected, you're out of luck finding a back court player to fill in easily. (If the pick is say, the Lakers that the Suns own this year and it's 14th or 15th - you can find a back court defensive guy pretty easily in theory - Franklin, Oladipo, McCollum, etc). It's a short-sighted move, for sure. So I see both ends of it.
Other reason, Woodson may really want to forge ahead with the 'Big 3' together and then Dudley would be rendered useless and JR/Iman can be swapped in and out depending on match up/flow.