Sounds like quintessential trade deadline bait to me. I would think it's much less likely to happen in the offseason. I also tend to think that such a trade is a lot less likely to happen now after the Washington trade, because a) Krivsky would take an enormous amount of heat for something that would be perceived (note that I said perceived) as a similar deal, and b) that trade, said to me, at least, that Krivsky wants to hang onto Dunn (don't forget that one of the first things he did was give him a contract extension as well), and I think Harang is even less likely to go than Dunn.
Apart from that, though, if Krivsky hangs around for awhile I would not be surprised to see him make a fair share of deals like this. I don't think he's afraid of prospects and I don't think he will cling too dearly to any player who's making tons of money if he can be even nearly replaced at a lower cost. This is taking into consideration both the ballclub he helped manage before and the financial constraints of the one he's managing now. I think this is a good thing in theory...I just hope he finds good enough prospects to justify it.
edit: Wow, I said "less likely" three times in that first paragraph. Freudian...maybe my optimism is waning.