The trick to doing black and white with digital is to use the "Black and White" adjustment in Photoshop so that you're not just doing a straight grayscale conversion. That gives you much more control. Then it also helps to add a tint to the black (I like to do it as a monotone, or even a duotone), so it's not a straight black, but a warm or cool black. That is how you keep it from looking plastic and lifeless.
Now I generally shoot film when I do B&W. I enjoy the process more, and it gives me more options to print them. I can scan them to post, inkjet print, or create a negative for alt. process, or do a silver gelatin, which I can't really do with a digital photo (the silver gelatin part). I also like the look of developers and the look of the grain.
In reality, I almost never shoot black and white from a digital camera. I will, however, do some processing to desaturate the image to near black and white, but leave just a smidgen of color information to give it a bit more character. I like it to look like a black and white image when it's next to a full color image, and only really see the color when it's next to a black and white.