In theory, I agree. I've often likened code development to muscles; you get good at what you do, and what you don't do atrophies. If you push changes ever hour, you get very good at making sure that works. If you push them every three months, you get good at pushing them every three months, and panic when something requires you to move within days. And so on. This applies to all sorts of development process aspects (test a lot, get good at testing, fail to test, becomes impossible to test later, etc).

In practice, neither what tedunangst nor I think matters, because once you ship something to a customer in any way, they're not going to upgrade it. Offer automated upgrades and they'll demand a way to turn them off. It's not just developer boxes we have to worry about, unfortunately.