With B&W film, I would use a red filter to get more contrast in shots that have a lot of clouds in them. If I don't use that red filter, as is the case with digital, wouldn't the detail in the clouds then be over exposed, and the info lost? With B&W film I could always burn them in, but with a digital camera or slide film, once the highlights are lost theres no way to get them back. So with digital, how would you be able to get the contrast that a red filter would give you with B&W film?
The short answer is: No. All a red filter does is blocks green and blue light. With B&W film, this would help increase contrast, but this is unnecessary with a DSLR. The photosites on the imaging chip already have color filters over them, so using a color filter on the lens to increase contrast is completely unnecessary.
Optimum exposure with digital is simple; shoot RAW, and expose for the highlights. If you blow the highlights, you are screwed, but you can pull a LOT of detail from the shadows in 16-bit mode.
Once you have a properly exposed RAW file, open it in your favorite RAW converter in 16-bit per channel mode (48-bit RGB) I recommend boosting the color saturation just a little beyond the bounds of good taste, but don't clip any of the color channels. Once you have the image in Photoshop, do any levels and curves you think necessary to get the basic tonality right.
At this point, fire up B&W Converter Pro, and now you have the ability to try out any color filter you like; red, yellow, green, cyan, or anything in between. Then you can custom-tune the color response to match Tri-X, T-Max, ilford FP4, or to something that doesn't match any B&W film, but works the best for getting the desired tonality out of the image. (This is why I recommend oversaturating the color slightly--you get slightly finer control when adjusting the color response here.) It's like being able to re-take the shot as many times as you want with any combination of filters and film you can imagine, until you get the exact look you want.
I have 2 galleries of B&W images I created using this technique on my web site:
Cache Creek, and
Schellville Station.