I'm more on your side on a personal side, but think if Word 2k3 to 2k7 was an automatic update? All the support requests coming in.
The real solution is to do incremental changes in most cases. Though this is a bit troublesome for the whole "I control the code on my machine" thing. In which case you could rip out the updater
The problem with incremental updates is it's easy to convince yourself they're all beneficial. Most people won't leave your service or app if a new change is slightly annoying. Without attrition, you may not realize the change was essentially negative. Over time these build up and you end up with people that are essentially begrudgingly using your stuff. You can probably grind out a business that way, but it gets hard to upsell or introduce a new product that way. Death by a thousand cuts and all that.
