Steep gables are a key Tudor feature.

Homes in our neighbourhood were modeled on Tudor styles when built in the 1970s. Now, a generation or two later, affluent "modernizers" regularly come up with more and more hideous "improvements." If there's a steep gable they call it Tudor. Remove the gable altogether, if you like. Just don't call it Tudor.

Design all four sides of the house at the same time and put the same amount of effort in each side. It is a sculpture not a painting

I like it except for the stone on the lower part. Having 3 different cladding materials is too much, especially on a small house, and especially since they are all different colors.

You’ve succeeded in dropping a suburban new construction neo traditional home onto your historic cottage. Get rid of the extra trim, corner boards and lap siding are enough. 12/12 roof is way to steep, 6/12 ish is enough, like the current house and the neighbors. The gable should have the same eave height as the main structure. What are the interior ceiling heights? In the render it looks like you are trying for higher ceilings on the second floor than the first. What you have designed is fine but not good.

Keep it simple but larger instead of trying to make it something it never was.

The stone is original and looks good in real life. The mock-up makes it look like cheap cladding. I don't think the Tudor white boards look good. I'd remove them and keep the rest. I'd remove all the white boards that aren't window trim. I'd keep the gable with the same siding as the rest of the house.

In the mock-up, the color of the siding doesn't go with the stone or the cedar in the gable.

I'm not sure you want a portico roof that extends over the bay window or a flat roof over both the porch and the window at different heights. That leaves you with the sloped roof over the window or redesigning the portico. Because of the window above it, you probably can't have a gabled roof.

I've tried to show bringing the 2nd floor wall out even with the wall below, eliminating the roof over the bump out

And I might consider a tall frieze.

Change the muntin pattern (shown in the tripple window) in the small windows giving the individual panes better proportions.

Cute house, I love Tudors! The shingles in the gable, the portico with pillars, and the gable returns don't fit with the Tudor style, in my opinion. I think a continuous shed roof across the front, over the porch and front window would look much better.