Help with Exterior Facelift on Ugly Mansard 5 Plex

[Kirk Koskiniemi]

I am rehabbing a nasty 5 plex I bought last fall (pics at bottom). Besides redoing the entire inside, I plan to paint outside, install new cedar/cable railing, redo roof with metal, replace doors and windows, paint, and remove and replace landscaping without big trees. (I know, it's a lot). Question- what is the best thing to do with a Mansard roof design like this TO MAKE IT LESS 1970s? Should I paint each unit seperate colors? Try to dress up the windows and doors with some better trim? I have a sketchup drawing below of the direction I'm heading (disregard the colors, I'm not great with the color selection of sketchup). What do you guys think? Am I on the right track with the general sketchup design, or does it look horrible? Again, disregard the colors. If you want to add color advice, I'm down with that. Thinking of a charcoal gray metal roof.

[Kirk Koskiniemi]

A picture of the flat roof done. I own a roofing company so I do the Durolast roofs frequently.