Everything you are thinking about is perfect! Add new gable garage doors, a pergola or arbor above with climbing roses or like, a new brass house numbers plaque, much larger windows with decorative shutters and a glossy lacquer front door with great hardware, brass kick paler and or a knocker is a must! What fun you'll have!

Some more ideas, I would make that circle above garage stand out as a feature

Should I paint the brick, if so, what color would you choose...

The consensus in houzz seems to be to leave brick natural because of the maintenance with painted brick. I love the look of natural brick.

Once you get your larger windows, you may like the look of the house, without having to paint the brick (which I like). I would though consider instead of a metal awing, a small pergola over the door area to make the entryway more prominent and welcoming. A carriage style garage door would really update the house (and add a large coach light). You could also add a non-invasive vine that eventually will fill in the blank brick area.I think you home could have a quaint English type feel to it. [houzz=]; [houzz=]

I don't think I would paint the brick work, I like it, do the other things then see