Ever since I got my Mac Mini I've been struggling with the printer issue. I have an Epson 2200 hooked up to a Windows machine. It took a fair bit of research to figure out how to connect to it from OS X, but I finally managed it. It is supposed to be easy, but it looks like a lot of people have problems. But I could only use the Gutenprint (formerly Gimp-Print) drivers which don't support all the features of the printer.
I downloaded the latest Mac OS X drivers from Epson, but I couldn't see how to use them. Finally I found out that you can't use USB drivers on a networked printer. This seems like a strange distinction - on Windows I can use the same drivers whether the printer is connected directly or networked. Maybe it works if the printer is shared from another Mac - I don't have two Mac's to try it.
I thought a network print server might do the trick but from what I could find out, I'd still have problems. It looks like Apple's new Extreme Air Port might handle it a bit better, but it still wouldn't let you run the Epson utilities (ink level, cleaning, etc.). And although they claim it's Windows compatible I wouldn't be surprised if there were issues.
In the end I physically moved the printer and connected it directly to the Mac. Rather than fight with sharing it from the Mac and somehow connecting from Windows I just went out and bought a new printer for the Windows machine. (I wanted the large format 2200 on the Mac since that's where I plan to print photo enlargements from.) I bought an Epson R260. (Epson's may or may not be the best, but I'm familiar with them.) It amazes me that a printer that has a resolution of several thousand dpi and produces 1.5 picoliter droplets costs only $120! I realize they make their money on the ink, but it's still amazing price/performance relative to a few years ago. Of course, I'd like the newer Epson R2400 to replace the 2200 but that'll have to wait.
It seems strange that Parallels and VMware can virtualize an entire computer, but for some reason OS X printer drivers are tied to hardware. I'm sure there are "good technical reasons" for this, but it seems pretty crappy to me. The Mac seems to lose to Windows on this front.