www.ninite.com/accessible

It will make an executable that will automatically fetch the latest version of various software packages and install them for you in the background. The only window you see is the Ninite window and the only button you have to press once it runs is the close button once it is finished. Using it is simple, it's perfectly accessible. Go through the list of software on the page, that link goes to the specific page listing the supposedly accessible software, and check the boxes for the software you want to install or update. Press the "get installer" button and you'll get a download of an executable file of around 250kb.

The Ninite executable will install software you chose if it isn't already installed, or update software if it is. It checks if you already have the latest version so it won't waste time on reinstalling something you already have up to date. It automatically says no to desktop shortcuts and google toolbars, it's also free. On top of this if you keep the executable you can run it any time and it'll always fetch the latest version, so if you run the Ninite installer a year from now it'll still fetch the latest version of NVDA for example. It's great for annoying software which tells you there's a new version but insists you install it and makes you install it as if from new, cough, iTunes, cough. The software it supports includes:

NVDA, yup that surprised me too
Chrome, not on the accessible list but it's on the main list at ninite.com
Firefox
Thunderbird
Flash for Internet Explorer, probably the most accessible way to update flash
Flash for other browsers, see above
Adobe Reader
WinAmp
Skype
Java
7Zip
iTunes for Windows
.net framework 3.5

Hope this helps someone. I certainly find it a lot more convenient. There's a paid for updater as well but all it does is ask if you want to run the update when there's a new version, most software checks for a new version itself anyway even if it doesn't install it so you might as well just use the free version.