Quick fix: I would put a nice post at the top of the steps to the front door and replace the metal railing. I assume the small windows under the pitched roof are for a bedroom, but it would be nice to see that window the same height as what looks to be the living room window. I assume the door is painted the same color as the pitched roof. Maybe just the same color as under the living room window. Nice looking house you have.

The bay window treatment needs to be addressed. Moving the shingles next to the door over to the bay area would be a good start. I'd go with stone veneer or batten board to replace the shingles. Love the door for now- sorry, kids!
The craftsman look will need a whole new roofline and windows. I'd probably try to add a second floor master with that project and get rid of the ridge and bay window. Really need to know the floor plan to advise on that, but if you don't plan to move the entry, you might incorporate a Craftsman type of siding by the door now.
I think the foundation should be a darker color (gray) to ground the house. I like the contrasting color in the ridge, although I would probably go with a different color since the door is yellow. I suppose you could repaint the door and make the kids happy. :)

Thanks for your ideas! This is somewhat of an old picture as ive painted the peak the same blue of the house now. I plan on ripping out the ugly railing and yes, adding a post might work. I hate the white around the Bay window, was thinking of river rock veneer. The smaller window is the current master bedroom but adding a larger window might help balance it. When I do the addition it will consist of a new master bedroom and bath on a new upper level.
I painted the door yellow, maybe black? I think the yellow adds a bit of country charm. Was also thinking of putting slate tile down on the front steps or that rollable stone? Or, perhaps rip them out and add a porch?

Love a yellow door on a blue home!
The bay window is more Victorian in style than Craftsman, so I wouldn't call to much attention to the feature by giving it a different siding treatment than the rest of the house. The river rock would look great next to the door, with bluestone on the stairs and landing. Still, if you plan on major changes to the entry, I wouldn't invest too much now.
Find out what's realistic structurally in terms of adding a second story, then you'll know exactly where the porch will be and you can work from there.
Sweet house- best of luck with your plans!