Should the Cubs now see if he's amenable to a short term, high AAV deal?

Maybe.

The thing is that because the Braves made Bourn a qualifying offer, he will cost the Cubs a high 2nd round choice. With the new CBA and compensation system, that is roughly equivalent to what a first round supplemental pick has been in the past few years.

The Cubs would have to be reasonably certain they could get a prospect that is of higher quality than what has traditionally been a 1st round supplemental. In other words, a pitcher better than, let's say Pierce Johnson. Or at least a Johnson type prospect plus another player.

That's risky. What if Bourn regresses or gets hurt? The Cubs lose that potential to flip him and regain any value. The Cubs have a bird in the hand now with that draft pick, should they be quick to flip it for two in the bush?

I'm not so sure.

The other argument for signing Bourn is simply to make the Cubs a better team, but honestly, Bourn has been a very good player, worth about 4 wins per Fangraphs over the past few years, but is he a difference maker by himself?

Even if he manages to sustain that level of performance into his 30s, how much does that help? Moreover, it wouldn't even be 4 wins since he'd be replacing either David DeJesus or a Nate Schierholtz/Dave Sappelt platoon. Either way it should worth around 2 WAR. In other words, it's likely to be about a 2 win upgrade, 3 at the most.

Are the Cubs 2 or even 4 wins away from being a contender? Probably not. It's possible, but it hardly seems worth the risk at this stage. Perhaps if there is some more movement on the roster, such as a trade of Alfonso Soriano, I may change my mind on this. Right now, though I know many will disagree, I just don't think it's a wise move for a rebuilding team.
http://www.chicagonow.com/cubs-den/2...-legit-option/

Pretty well sums up my thoughts better than i was doing.