Seems like it would be useful if the GUI client had an option similar to the bitcoind "sendfrom" functionality. Do you think this would be impossible to try and get into the client? Am I just wasting my time? I'm willing to do the work and write some code for review, but I don't want to go down that road if it's something everyone would basically vote down at review time.
I wouldn't have any objections to changes that let you decide which input transactions or receiving addresses to choose when sending coins, as long as it is well-tested, follows the coding guildelines (see coding.txt in the source directory) and it doesn't make the "I just want to send some coins" case look more complicated (maybe hide it behind an Advanced... button in the Send dialog).