One big ease-of-use advantage Linux distributions have over Windows is the process of installing and updating applications - thanks to repositories and software like Debian's apt-get. Running Windows doesn't mean that you can't easily maintain your app installs. With a few helpful (and free) downloaders you can add that missing functionliaty to your system, too!
Here are five that I find particularly helpful - share your favorites in the comments!
Anti-Malware Toolkit (pictured above) - If you download malware fighting apps frequently, you need AMT. Nearly 40 programs are supported, including must-haves like MalwareBytes, CCleaner, Autoruns, Unlocker, Rootkit Revealer, and more. AMT also supports command line arguments for easy batch scripting and scheduling.
FileHippo Update Checker - FileHippo is one of the best places out there to download software. The site is well organized, and they do a good job of only listing quality apps. Their update checker makes it easy to keep your core free applications up to date. It's also available as a portable application.
GetIt - Wondering why AppSnap, AppUpdater, and Win-Get aren't listed? It's because GetIt rolls all three into a single interface, is able to download over 400 applications, and integrates nicely with FARR. Don't worry about installing the supporting cast ahead of time, GetIt will grab them for you on the first launch. GetIt is also portable now, though you'll need to install the regular version first then create the portable file yourself.
Chrome Nightly Updater - If you prefer to rock a cutting-edge (and unstable) browser, nightly builds are the way to go. CNU makes short work of keeping your Chromium install hot-off-the-compiler fresh.
Ketarin - Are you the hands-on type? Ketarin is the downloader for you - think of it as a kicked-up frontend for wget. Since developers can frequently change folders and filenames (hello, version strings!) Ketarin can be a bit of work to maintain. It's not all DIY, though, as Ketarin also supports FileHippo program IDs - which never change.