Basicly there are three primary softwares used in the print biz:
Photoshop, Illustratrator (Avoid version 9), QuarkXpress
QuarkXpress may not be the best it could be, it is however the defacto statandard for page layout/publishishing, every publisher and prepress houses most will support it.
Indesign also looks very nice, but you may find some print houses and prepress shops my not take it quite yet. It is gaining quickly as few are happy with Quark 5 as it added very little that 3rd party plug-in could not add to Quark 4.1.
Pagemaker and Freehand are also common, but most shop using PageMaker have switched to InDesign. Freehand may be a wise choice if you are doing both Flash and print graphics.
In eather case you will may also like to buy adobe acrobat, more and more shops are requesting PDF files. In most cases the safest way to generate PDFs from Quark is to print using the adobe ps driver to a file or direct to the Acrobat distiller driver. I believe InDesign ships with distiller as does Pagemaker.
You will also need Fonts, I avoid True Type fonts when possiable, it is scary at how old some to the equipment is at smaller shops and it is just safer to stick with Postscript fonts. (But this highly depends on you printer.)
I also find a Mac is almost mandotory, not so much for the applications but I am constantly encountering font issues when sharing files with designers and print production people.
Have just gone freelance, I've had real problems not using a Mac, so much that I plan to will to dual lience Illustrator and Photoshop and switch to Mac. Lucky I mostly do Photo montage, retouch and color correction work in Photoshop so font are not often required.
As for a printer:
Unless you will be doing images only, It should be Postscript capable, either with software or hardware. I would recomend tabloid size, I have been looking at a HP1700ps, it is targeted at the small designer and looks adaquate for the price. As for color proofing, you are not going to find much that is truly reliable (with out a lot of work) for proofing images for press for under $10,000, even the Epson 5500 sucks at calibration unless you spend the bucks and by the splash RIP and then is only mostly sucks.
All print work will pass though a Postscript RIP as some point and you will need to make sure your file will print correctly. Most printer will require a composite proof, and a seperated proof meaning you will need to provide a print out each seperation ie. C, M, Y, K and any spot color, this is primarly to check overprints and knock out problems.
(Note: If you dont have a Postscript RIP, you can send the file to Acrobat distiller and then print the distilled .psd file using Acrobat Reader, it adds a step but you may need to generate a PDF anyway.)
You should also get yourself a copy of Dan Margulis'es Professional Photoshop, this is simply must it goes over almost everything you will need to know to prepare images for print use. I can stress this enough. read it cover to cover it will save you money and pain later.
J. Stuart J.