As tasks get longer / more complicated, I find myself leaving things unattended a lot. Software installs are a good example of something that are often left alone. In this regard, most installers are decent about getting the meaty info up front, and then just churning away on their own.
One of the things I've been after lately, thanks to blowing my download quota last month and being shaped to 64kbps for eight days, is scheduling downloads to run in the 1am-7am "off-peak" time. But this is not an easy thing to do ...
Take iTunes. It checks for podcasts, and starts downloading them. But it has no scheduling ability, it just goes for it. You can pause, but then how do you resume? My solution was Quicksilver, and the handy "run at" command. So I queued up all the downloads, quit iTunes and then had Quicksilver re-launch it at 1am and the downloads all kicked off. In Windows, the Task Scheduler will do the same thing for you. I could've done something similar by pausing them and having an applescript resume them at 1am, but again it would've had to have been started by a third party program. I want scheduling in iTunes, but at least since iTunes doesn't ask any questions, this is very easy to kick off and leave unattended.
Now take something from Blizzard. They've released the teaser cinematic for their latest World of Warcraft expansion, Wrath of the Lich King. I wanted to download the HD trailer, and they offer a customised bittorrent client called the Blizzard Downloader specifically for the purpose. Brilliant. I started it up, selected the save location, then once it had allocated the space and created the partial download, I closed it. Now just because I always like to test these things, I had Quicksilver open the downloader again after a delay, just as I would if I was scheduling it for post-1am. It opens up ... and asks for the save location again. Fails the unattended check. What's worse - when I chose the same location, it didn't resume, it overwrote.
Sticking with the gaming side of things - the Warhammer Online client also requires authentication before you can patch. Perhaps this is because at the moment it's a beta, and you need to accept the beta test agreement every time you log in, but it's still incredibly frustrating, especially since beta games patch frequently, and are often relatively large patches too.
Sure, there are other issues at play here. If Australian ISPs weren't so damn stingy, we wouldn't be so focussed on off-peak time. But for now, it's what we have to work with, so it would be nice if software was obliging!