Paint the house , get rid of the shutters and get the doors you are thinking of.

Exactly what is "Craftsman" about the house? Stop agonizing wait until spring, consider a new paint color, when you can see the roofing color, but mostly save money until you can address the entire unsubstantial entry focal point, stoop/steps etc. And an architect for a more significant update.

I'd go with a brighter blue.

Yeah, those shutters are silly. They need to be twice as wide as they are.

The bright white garage doors are saying, “hey, look at us!!” They should either be the same color as the house, or a coordinating, subdued color. Or wood.

I believe this house is more colonial than craftsman. Google for an appropriate colonial style front door sample. A bigger, roomier approach to the door is desperately needed. I can’t tell how big that miniporch is, but it’s not nearly big enough. And a half-barrel portico over the door would be great.

P.S. You would probably get a lot more replies if you post this in the Remodeling Forum, too. Or maybe even the Landscaping Forum. Not many people visit the Windows Forum.

Overall, it s a lovely house. I find nothing wrong with the windows and would keep them. Adding new garage doors with windows would seem too busy a look, competing with all other windows on the front of the house, so I would keep them as is. Don't make them more fancy than the rest of the house. The eye should go to the front door. I love the picture you posted for a new front door and is a nice, easy and generally not too costly way to make a quick update. My preference is always to have a roof over the front door, and I would work with an architect who could come up with some ideas for that. And the stairs need a handrail. Yes, wait to see what colors would go with the roof, the blue is pretty but perhaps the owner would prefer a more sublte color. Good luck!