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Sideload means copy via USB, but actually any method (Mobile, WiFi, BT, SD card, USB) that's not a direct internet connection to the store of the company selling the ereader or suppling an app. Not all makes of ereaders have stores. You may buy ebooks or get PD ebooks from other than Amazon for a Kindle, then you can only sideload them. You can also sideload ebooks bought from Amazon that you first downloaded in a browser from the Amazon account.
Jailbreak is the process of making a Kindle or Nook able to accept user supplied settings not otherwise possible, or add 3rd party applications. A Kindle out of the box is like a VHS, CD player, record player etc, it only allows what Amazon has decided.
An iPad or iphone currently need a jailbreak to bypass Apple's store, but EU is fighting Apple on that. Most Android devices can install 3rd party APKs, bypassing Google's Playstore without a Jailbreak, but need one to install an alternate OS.
Kobo and many other ereaders (apart from Kindle and Nook) doesn't need a jailbreak, but there are few third party apps. Even if that wasn't true, the Kindle is more restricted without a jailbreak (inability to set series, collections, subtitles etc from computer/Calibre, but Kobo lets you set all those).
Mostly a new Kindle can't currently be jailbroken. Unless a new exploit is found, but then Amazon updates the firmware and if you turn on WiFi, ever, eventually Amazon forces an update. You need a Jailbroken Kindle to be able to install earlier firmware. Kobo models generally can install any earlier FW as long as it's not earlier than original for than model.
Like a VHS, or microwave oven, the Kindle is fixed in what it does without a jailbreak, which might not be available.
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