The Basics - I need iTunes Match for Dummies

Been using Macs forever but this iTunes Match is a beast. I have less that 25,000 songs. Lots of these are tracks from Audiobooks uplaoded from CDs but the rest is what I have put on itunes from my CD collections and a relatively small part is purchased from Apple.

iTunes match sounded like a dream! I could have access to most of what I wanted without loading GB's of info on my iPhone and the iPad on order.

But now it hangs on step 3, I have to worry about crossed out clouds, no clouds, double crossed out clouds, "not elligible", bit rates. AAC and mp3. (My favorite was the advice to use advanced control to change inelligle songs to AAC. All I saw was the option to convert to MP3, which means it is already AAC, right?

So I think, what need is iTunes Match for dummies. Step by step. What to I do to make sure my library is ready? How do I fund what needs to be converted and how do I convert it? How long should Step 3 take?

In short, is it just me or is Apple losing it's right to be thought of as "The computer for the rest of us?"