I'm not sure what to make of questions like this. Just experiment with different amounts of swing and see what happens. I would almost guarantee you that's what Rodriguez Jr. and Stimming are doing.

Guessing the track ID used to be part of the fun!

A few of my friends who switched to DJing with Ableton or Traktor have gone back to using Technics. I imagine Hawtin will eventually crave the manual beatmatch again just like they did. Personally, I'm considering an S4 or some V7's, but I don't ever plan to ditch my Technics. I'll probably go with ...

This one is good for old mixes.

http://soundcloud.com/fxxp

Is it possible to sidechain?

2 Live Crew - Throw The D

I think CBR is better for DJing, but I use control records. As far as bit rates go, I prefer 320 but won't hesitate to drop a track as low as 224. If it's a DJ mix, I usually do it at 160 or even 128 to keep the file size down.

Go with Audacity. I think most will agree that it will get the job done.

I use Audacity most of the time. iTunes also seems to do a good job.