Hey Areality..
I do believe we are in similiar positions.. trying to make sense of the whole new world that is B&W...
From one newbie to another, these are what i look out for:
1. Composition.. Self Explanatory
2. Contrast.. frames with a wide range of tones make for great B&W Shots
3. Form... For e.g, a silhouette of a person, etc etc
4. Pattern.. Look for geometric patterns in the subject and zoom in close enough to feature the pattern prominently, without losing the viewer to the fact that it is a person.
Yep... Actually, for the conversion of Colour to BW, I prefer to use the Colour Channel Mixer Filter in PS.. For more info regarding BW, perhaps you can try and find the May (i think) copy of Practical Photography... its on shooting in mono,
Alternatively, National Library has a lot of stuff on BW.. especially at the library at Taka i think.. that day i went, i was surprised at the number of books about BW Photography.=)
Hope this helps!
Cheers