I would remove all the added trim work every where except on the garage doors. I love this color with brick and I think it would look great on your place including the garage door . Notice how th trim and the siding are all one color Make sure those areas under the windows are also done. Get rid of the overgrowth to the left of the entry so you can actually see the front door and maybe a nice glass and metal post and railing . You could try just anice deep bed in front of the porch side on the right of the steps then a nice lower growing plant on the left or a really nice pot filled with seasonl plants in that space on the left .A taller pot between the garage doors and maybe a nice janese maple for the front yard.

Fix the landscaping next to the stairs.

Tear out that evergreen and replant with items that will cascade over the edge of the concrete.

Here are some Tudor paint color schemes.

Can you post some pictures what you mean by classic creative? Do you want to keep the Tudor trim? I would remove it, or if that's too much fuss then paint it the same colour as the background.

I would paint your siding, garage and trims in a fairly dark colour because your brick is quite dark. I think it would blend attractively. I don't think you want to emphasize the different proportions of brick, siding and garage door.

Your front door could be something lighter to stand out. I'd add black railings to the steps for safety and also a more welcoming look.

As for landscaping, start with evergreens. For recommendations, what is your closest big city? Which direction does your house face? Evergreens come in different needle colours so yours would look more interesting than my mock up. Could we get a picture of your front porch area? It's hard to see what is there.

Remove the grids if possible from your windows.

Here's a pic that gives you an idea of what I mean. I used Sherwin Williams Urbane Bronze, a popular colour for outdoor applications, but of course you'll want to do test boards as it would look different on your house.