Reply to Advice for setting up

Hello all.

A little background on me: I've Dj'ed professionally since 1990, however I took a break of sorts for the last couple of years. I come from the world of 1200's, Dennon, Pioneer, and Rane gear playing electronic dance music. I have iTunes, but there is very little of my music stored in it. For the most part, my music collection consists of records, CD's, self made CD copies, and an 1TB external drive of .wav files. When playing out with CD's, I use SKB cases, and keep my music alphabetized by artist with a separate section for compilations.

I Just purchased a Kontrol S4 to be used currently with my PC desktop, and when I am ready to play out with Traktor, I will be purchasing a PC laptop. I know the benefits of Mac vs. PC in a sound environment, but this simply is not going to happen, so please don't waste your time explaining it to me.

The advice I am looking for is what your opinions are on how to set up my music libraries for use in Traktor for the first time. I would like to save the work load of trial and error and have things set up in a logical format. Specific questions I have are:
1. Should I use iTunes for cataloging my music? I have many (over 10,000) songs from vinyl that have been converted to .wav files, put in folders and categorized, and then burned to CD. What is the best way to convert these songs to MP3 format to minimize typing? Is there any song recognition software that I should know about?
2. If I go with iTunes, is it possible to set up BPM and Key information (or is that something that Traktor does?) Is there any BPM or Key software that I should know about?
3. When importing playlists and such into Traktor, is there any structure that you have found that proves to be logical when searching through music for "that one song."
4. What about cover art? I know you can get cover art for songs purchased on iTunes, but what about other albums not purchased from iTunes, records, and CD's?
5. Any other advice or insights would be greatly appreciated!

Please keep in mind that i will be moving Traktor to a different computer at a later date, and I do not want to take an external hard drive with me while I am gigging. I look forward to everyone's advice.

Ryan