It really seems that Microsoft has never cared very much about this aspect of the user experience. I can't tell you how many systems I've encountered where Windows Update was completely botched after a fresh install for no reason at all.
A guy at work just bought a secondhand laptop with Windows Vista on it. He doesn't need the laptop to do very much (just run the Chrome browser). It was infested with spyware, so he asked me to do a factory restore on it.
The factory restore process goes smoothly, but the HP bloatware was horrible. I uninstalled most of the bloatware, temporarily killed the Windows Update service, and connected to WiFi. I planned to save a lot of time updating by just downloading the offline installer for the latest service pack, and then just download the supplemental updates through Windows Update. Well, IE7 doesn't work on almost any web pages. It keeps showing an error message dialog saying something like "operation cannot be completed" after the page loads. After dismissing the error message, the page that was already loaded is replaced with an error page saying that the page could not be displayed ("check for network problems," etc) - a completely inappropriate error page. I know IE7 is old, but every page where I try to download IE9 or SP2 fails with the same error. I can't even download Chrome or Firefox.
Well, I happen to know how to download Firefox via command line FTP or explorer.exe's FTP support, but I resolved to find a way to do this without using third-party software and without shuttling files from another PC on a removable drive or disk. Well, after trying for waaay too long to download SP2 or IE9, I eventually gave up and spent countless hours installing updates through Windows Update. You know the drill: Check for updates, install them, restart, check for updates, ...
Finally, Windows Update is trying to install a service pack update...but it's SP1 instead of SP2 (?!). OK. So I start installing... Being a major service pack update, it launches its own installer with warning / agreement and a message saying how long to expect the process to take. It also warns that there will be multiple restarts. Well, just a minute or so after starting the update, it disappears and Windows Update dialog says the update was "installed successfully." I restarted the computer. System Properties still doesn't indicate any service pack is installed. I checked for updates and it wants to install SP1 again (even though it already appears as "successfully installed" in update history). After a many rounds of this, my history of installed updates shows SP1 over 5 times, each saying "successful." At this point, Windows *still* wants to install SP1.
I finally relent and download Firefox via FTP. From Firefox, I download/install Chrome. From Chrome, I download the offline install for Vista SP2 32-bit. It runs, but demand that I install SP1 first and exits. It's like Microsoft forgot that A SERVICE PACK SHOULD ROLL-UP ALL OTHER UPDATES BEFORE IT, INCLUDING PREVIOUS SERVICE PACKS.
I download SP1 offline install. Installs fine with no problems. I run SP2 install and it says I need IE9 a newer version of IE. Internet Explorer keeps directing me to Microsoft download pages that have no choice of x86/x64, but it keeps downloading the x64 installer for IE9. Once again, I have to use Chrome. After getting IE9 installed, SP2 finally installs.
Now I'll probably have to install dozens more updates to be caught-up. I couldn't get this far without third-party software or shuttling files from another PC. Way to go, Microsoft.
There's still the massive annoyance that this Synaptics touchpad moves slowly in the horizontal axis and quickly in the vertical axis. It's nearly unusable. The Synaptics software doesn't have a way to compensate.