Pressey is both a pure PG (the only guy on the roster besides Rondo who can be classed as such) and a good ball-handler. Crawford, while not a pure PG, is a capable ball-handler. I'll agree that Bradley isn't good at the point guard spot, but I don't see him as god-awful in very limited minutes. That said, Rondo's only going to be out for a few months at worst and the team's not expecting much success this year, so if they lose a few more games than they would with a more experienced point guard in the interim... oh well. It's one thing if Rondo were out for the whole season, but he's expected to come back at some point. This is a temporary fix to an issue that isn't all that pressing, imo. Not to mention, the shooting guard spot needs to be cleared up at some point - best way to do that is by showcasing all of the guards by playing them as much as possible and it's harder to do that when you add options at the point guard spot.
Barea is a spark off the bench? I agree - but theoretically, so are Crawford, Brooks, and Wallace. Barea's contract runs until 2015, so you're giving up a first-round pick just to get out of the last year of Wallace's contract to have Barea serve virtually the same role as Wallace. Of course, Barea would be doing that for less money, but again, what exactly is the cap space going to be used on? If we're realistic about the rebuild, it's going to last quite longer than a year, so does it ultimately matter if Wallace is on the books for now?
The look at Cunningham isn't going to be very useful. He's a combo forward, but he's more geared towards PF play - the same position where the Celtics are looking to develop Olynyk and Sullinger.
And Bogans is a shooting guard. He can play small forward, but he's a third-stringer guy at that position; hell, he's a third-stringer even at his natural position. Not exactly the player you want playing significant minutes at the 3.