I think this:
One can make digital look like B+W film. But, the more important questions are:
1. Can you simulate a 'film look' that you like? There are a lot of film shots shown in this thread that i would NOT want to emulate. Everyone does it differently, and there's a certain amount of grain and a certain kind of tonality that each person prefers. I've been working on a sim that's closer to Rodinal+Tri-X (Ellen von Unwerth, Ralph Gibson, etc.), where there ARE blown highlights and filled in shadows.
I also like a sort of 'half' Lith look, where it's not necessary to end up with the dynamic range people accuse digital of not having.
2. After the image has been 'worked on,' can you look upon it with satisfaction, and not think that you cheated or faked it? That is my chief issue at the moment. It's getting better, though, as my memory is not so good, and if i leave a picture alone for a while, i can sometimes forget what i used to make it. But, if i do remember (or check), i hate that i think of a simulation as a fake. I have a prejudice against digital, even though i love the immediate feedback.
I also think many people process images 'incorrectly.' At least, i used to. I would take a digital image, make corrections and adjustments, and THEN apply a film grain simulator. But, if it had been a scan, the grain would be baked in and would also be subjected to all the processing. So, now i start with a very flat RAW image, apply grain, and then work on it. The grain seems much more integrated. I also use multiple layers of different grain. What happens is that the out of focus areas react differently than in focus areas. Areas that get different amounts of light react differently.... It's not a quick and easy process, but it gets me closer to 'authentic.'