There should be a gap, and there should be flashing (step flashing from when the roof was done) in that gap. The gap is to prevent the wood from wicking moisture. It also helps prevent any roof debris (leaves, catkins, etc) from getting snagged on the siding and junking up the transition. Debris can cause rot as well. It's not easy to make the clean-up cut. I've done it with a small battery powered circular saw, set to a depth slightly less than that of the siding. You do not want to cut into the flashing. I laid a length of wood on the shingles to act as a fence, or guide. I then ran the edge of the saw's baseplate up this piece of wood. It helped in maintaining a straight cut. I then cleaned up the cut with a utility knife. Again, be very careful regarding the flashing. And be careful up on the roof.

I think Sherwin Williams is the paint matcher for James Hardie, Id have them paint match for your brick bc artic white is a light mist color… I just put it on my house not knowing it wasnt true white and Im so upset… even the little sample looks bright white, but when it goes up its grey misty color. Wish I would have known!

If you wanted to add a porch roof to your home, you could use panels or porch posts on either side and than used recessed lighting in the ceiling for a porch fixture, so don't buy a fixture if you might add the porch? They are often overpriced and most interior fixtures with a lens over the bulb, work just fine in the porch roof....... I would paint your siding a pretty shade of white that is similar to your windows.., it's the best option given your dark color door and shutters and current roof... The house will look very nice and neat for as long as the current roof is there. Don't ever make your roof black. It will absorb heat and make your house very very warm.... Make it a medium to charcoal gray color(not a blackened gray either) for that color will reflect heat away from your attics and upper story.. The white of your windows & siding, and porch and shutters in the darker color will be very nice, and people will see your whole house in their vision field, not just a black roof.. If you add a porch, use 2 posts about 5 to 6 inches wide in each corner, and have them white as the color of your siding and mortar is. Let the pretty red brick and dark shutters and front door, stand as your 2nd and 3rd home colors. That's enough and will make your home have the most curb appeal likely.

If the whole house is siding paint the former the same