Windows only: Ninite, makers of supremely convenient one-click installation tools that you can easily share, have added a new tool: an update watcher that stays on top of Ninite's 92 supported apps. It provides the same no-hassle experience as their installer.
If you were starting a system from scratch, especially for someone without a wealth of Windows knowledge, Ninite could be a smooth ride. Pick out apps to install, install them all with no prompts or questions, then use the Updater to watch the apps, ping only when updates need installing, and only click once more to update everything. Because Ninite covers some of the apps more prone to security risks, like Flash, browsers, Java and others, it's especially nice to have an app watching your programs for you.
Ninite's Updater isn't free, but at $US10 per year, it's certainly worth the meter money for a computer you don't want to see fall out of date. There's a discount for bulk licenses covering five or more machines, too. If you were dead set on getting update coverage out of Ninite, there's a Task Scheduler work-around, but it will lack finesse and compatibility with certain apps' update protocols.