I'm staying up a little too late tonight over something that I think should be fairly straightforward. I bought myself a new Xbox 360 when I moved so that my girlfriend and I could talk over the Xbox Kinect Video Chat. Today, I set her up with an Xbox Live account for my old machine, and started the process of the license transfer and downloading my old content to the new box. Unfortunately, there isn't an easy way to do that.
The process is that you can request the license transfer to a new console once every 4 months. That makes any new downloads to that console available for you when you're offline. Unfortunately, for anything that you've already downloaded, you have to download it again. In my case, I've downloaded about 100 arcade games and about 200 other DLC updates (for things like songs in Rock Band and Guitar Hero). The download queue is only set up to handle 30 items at a time. So there is a lot of manual queue management if you want to download more than that. I just wish that there were a way that you could say "Download All" to the new console and be done with it.
The worst part is that I saw it was going to be a hassle, so I started breaking it down by download type, and did the first downloads by Xbox Live Arcade titles (which included add-on content for those Arcade titles). When I went to the Add-On content, it still included the Arcade title add-on content. So now, I have 5 years worth of content that I need to correlate between what I've already downloaded to create my queue. And if I exceed the limit of 30, I need to reload the web page (which resets the check boxes for what has already been downloaded) in order to re-request the downloads that exceeded the queue, making the management more difficult than it has to be.
Really, Microsoft? This is the best you can do?
The hassles with DLC are greater than the benefits from them. I don't forsee myself upgrading to the latest and greatest console in the next generation if they are DLC-only formats, just because of the ownership concerns. I really like the way that Steam handles things, so I am more likely to migrate back to the PC for gaming (which I already have in most instances).
Anyway, I am going to give up for the night (have also been running into DLC that is no longer available, for whatever reason), but have posted on the Xbox forums about my frustrations, as well. Please leave a comment below if you think that I'm being ridiculous (or if you agree)!