I'm not real sure where effort comes into play. I do think, at least where B&W is concerned, that it's a lot like comparing apples to hand grenades. Taking a digital file, even in RAW format, and converting it to B&W turns the recorded data on an RGB spectrum (I shoot in Adobe RGB) into an "equivalent" grayscale monochrome spectrum. It does this by weighting the values of the luminance with saturation in each color and applying the change based on a weighted proportion to the color data. The film emulsions and different developers each have their own response curve to the normal RGB spectrum and luminance. Unless I put a filter on the lens, I get the same response that range regardless of the situation.
I actually wanted to do a side by side comparison, but w/o knowing the response curve of the film it's really impossible to do a true comparison. I set my 5DMK2 and my Rebel T2 up on my tripod and took the same photo w/ the same lens (both are EF mount). I did an overexposed and an underexposed shot - both by the same degree. As I recall I shot at f/8 and exposed a half-second and a 10second exposure (ISO100, morning light diffused through my window).I did not keep the files after I looked at them. The highlights in the film scan were blown out by comparison to the digital file at 10s. There was a lamp shade in both and I could not distinguish between the lamp shade's edges and the wall in the film file as scanned. The difference in luminance on the stripes in my comforter was much more pronounced on film than it was in the digital (which was more "true to life") in its "straight" preset conversion to B&W. Where things got interesting was in attempts to equalize the images. I tried to push the digital file to look the same as the B&W file at 10s and I could not do it. Getting the lamp shade to lose detail to the wall to the same degree (at least to my eye) also made my head disappear and sent the stripes in my comforter into the nuclear range. I was able, however, to pull the film scan down to the digital file without losing detail in the shadow regions. Black was still black. On the underexposed frames the wall texture behind me was visible on film - though there was a strong vignette to the corners of the image (I was shooting a 50mm 1.4). The digital file had a single flat tone across the wall from corner to corner. The film was more true to form there as the shelves I have on the wall cast a shadow to the left of my bed and the light falls off to a shadow region to the right with a brighter circle in the center as a result. Attempting to equalize the scenes without knowing the response curve was equally impossible here. I also applied the same adjustments to each file. Knocking film scans down in exposure is far more useful than trying to pull pure digital down. I don't know why. Taking two stops off the digital files gave me very muddy shadows that appeared to not know what position they should take on a grayscale. Taking two stops off the film scans simply resulted in everything decreasing in luminance by two stops. It seems, by my limited anecdotal experience, that highlight areas hold *far* more detail in film than they do in digital.
Anyway there's a lot involved in the development of film that I think removes the ability for a real side by side comparison. I've already mentioned one part, but the other is the actual process of development. I don't know what the files I've scanned would have looked like if I developed in HC-110, Ilfosol 3, Rodinol, etc. instead of D-76. The same goes for the concentrations of each versus the stock mix of D-76. Ditto the temperature and agitation schedule. I'd assume the same goes for color, though I've not shot color film yet.