First they disobey copyright regulations and post-copyright one of their books (at least), which will make it appear less out of date in the future (fraud),

You miss several points:

• It takes time to print and ship a book, much less produce, edit, and write it.
• Copyrights expire at the end of a year, as far as they can be said to expire at all.
• Copyrights start at the point of creation of a work.
• The date in a copyright notice in a book is just a notice. Copyright protection starts from the origination of a copyrightable work, though it can be registered formally with the copyright office.
• I have heard copyright lawyers make the argument that a book published on December 31, 2003 would not receive a full year's copyright protection because of the end of year cutoff, so there is a year's variance in publication dates for book. I have not been able to confirm this in twenty minutes of digging in the U.S. code, nor would I take legal advice from the Internet.
• O'Reilly uses Founder's Copyright anyway.

I see in their latest catalog that they are selling a hacking book that sounds like it's geared to the scumbag variety of hackers

Spidering Hacks could be used to develop programs that harvest e-mail addresses, perform DDoS attacks, mirror sites without permission, forge information, crack authentication schemes, and other nasty things.

Then again, if you try to make it impossible for bad guys to do bad things, you'll likely only prevent the good guys from doing clever things.