I don't think Tony will be in very good shape by 2009 - that's over a year, so it's, like, four months in comicbook time. And he already misses Steve so much that it's starting to drive him crazy.

seanchai thinks Brubaker will bring Steve back in issue 50, because they like to have significant things happen in the 50th and 100th issues of a title (I suggest that, if they want something exciting for Captain America #100, they have Steve and Tony kiss).