Jailbreaking a Wii is quite complicated and it depends on what results you are looking for, you should first check your system version in settings - it will look something like:4.2E - then check whether that version is jailbreakable.
Google "hackmii installer" to download the latest banerbomb crack and follow the instructions on the website. After this your wii is jailbroker with the homebrew channel, with the homebrew channel you can launch 3d party apps from the sd card. The most usefull thing you can do with a jailbroken wii is run games downloaded from the internet from a usb flashdrive or hard drive. For this I use Wii Flow which is easy to install once you download it and follow the instructions.
Unfortunatley not knowing the system version I can't help you much more but if you search YouTube for "how to jailbreake wii (insert firmware version here) firmware" I am sure you will find may tutorials.
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You jailbreak the firmware.
Yes you have to jailbreak
yes,the 5.0.1 jailbreak came out !Official EasyRa1n Unlock/Jailbreak iPhone 4/4S iOS 5.0.1
At this moment you can't jailbreak the dsi. Refer to dsibrew.org for updates on it though.
The reason behind the jailbreak is sometimes theft of software (PS3 Games) and that is illegal.