Do you even like the shutters? To me, your home would look nicer without the upper ones. I like the dark brown color - you could also go with a warm blue, sage green, or burgundy if you want color.

I like the shutters. They add a bit of interest to the house. I would try and match the brown they were. I like the stained door.

I would remove the shutters from the arched stone window. The uppers...up to you. Just showing the house with no shutters.

Stain is always going to be less upkeep than paint on a door that has already been stained.

Even though it faded I would try to revitalize the existing color stain.

I like the brown shutters on your home.

When funds permit, get the small window in the front sized correctly so the front face of your home balances better.

I added shutters to the garage window.

The style of your shutters means they look better stained. If you want to change colors you should get new shutters, but I agree with the other commenter who said they shouldn't be on the arched window. Does your house face south? If so, this could be the cause of the premature aging of the front door. See if your painter has a recommendation for a finish that will hold up better over time. Or maybe the amount of sunlight your front door gets means you will always have to paint or refinish it more frequently. If you decide to go with paint and think black is too severe, how about charcoal gray?