Whew, ok deep breath. So you can get a wider rim in there, but not many folks have done one 5.5 inches. For a wired rim, a lot of times you won't see them labeled in inches, but rather in WM1, WM2, WM3, etc. The stock rear is a 2.15" wide, or WM3. The next size WM4 goes up to 2.5". All the graduations can be found on Buchanan's Wheels website.
The main stumbling block is working around things like lining up the chain and sprockets, brake hardware, etc. So in other words, there's not a idiot proof "kit" out there you can buy. It's just something you have to tackle piece by piece. Lots of measurements before you buy anything would probably be a good idea.