How much brick is on your home? Just the little bit we see or is there brick all around, and if so is it full or half wall?

I assume you will need to re-roof the whole house, and the whole upper storey will be new siding. Probably best to re-side the whole house. Maybe remove the brick or paint it the same colour as the new siding. https://romabio.com/masonry/

Just in the front ... what you see here

And a tiny in front of the truck

Half wall! Sorry

our roof is actually only 5 years old :( I wish we needed a new roof! I would love black!

I would go with the same siding as main body

am unsure how to advise you on adding space without seeing a floor plan or at least photos of other sides of the house. As far as updating the exterior the first thing I would suggest is replacing the columns at the entry. They are undersized and really aren't appropriate. The brick looks good enough that I wouldn't advise painting it. It provides a nice contrast to the siding. I would suggest replacing the garage door with one that has character. Would suggest installing one that has windows or lites in the upper portion. Garage doors with windows do more to alleviate a flat facade and give the house more depth. Good luck!

You will need an architect right from the beginning. What do you need the extra space for? What is your budget? I am not alover of bedrooms above garages .IMO the brick is the only thing I would keep and when the addition or not is decided I would remove the shutters and change the windows to no grids and a new door.

Paint and porch posts will make a large difference right away.