It's not really about automated checks to see if the hardware is up to the job or not... You're comparing PC (with massive storage like DVDs) to phones (that have to get updates over very slow 2G connections). Windows, for example, should work on any modern PC as it comes with a billion drivers and a huge number of abstraction layers (e.g. applications sitting on top of direct X, sitting on top of drivers, sitting on top of hardware virtualisation, sitting on top of more drivers, sitting on top of the BIOS, sitting on top of the hardware). It has the resources to make itself work on the vast array of hardware out there.
Android and mobile phone hardware are totally different beasts. Google released Android, which sits on top of Dalvik, which sits on top of a specialised version of Linux, which in turn sits on top of drivers and the hardware. So Google don't have anything to do with the people who make the hardware, and Android doesn't ship with a load of drivers to make it work on any hardware. It doesn't come with anything like that.
The hardware manufacturers, such as HTC, Samsung, Motorola, etc are the ones who have to make Android work on their phones. Whereas the OS vendor, Microsoft, are the ones expected to make Windows work on other people's hardware - or at least get it working enough to allow the installation of updated drivers.
So when you say Sprint is not wanting to invest money, in fact that should be aimed at Samsung. They're the ones who make a given version of Android work with a given Samsung phone. Once they had Android working, they'd then have to upgrade their customisations (e.g. TouchWiz, if the Moment has that, not sure) and Samsung apps to work on the new version too. Only then would Sprint have to do anything, and they would have to further work on it to add their own customisations on top of it (Sprint apps, and other minor stuff like graphics and ringtones). From what I can tell, the ball is in Samsung's court for the Samsung Moment and Android 2.2.
Samsung have a pretty bad reputation when it comes to supporting their phones. I just pray they don't continue this with the Samsung Galaxy S range of phones.