Chiflipper is right. Repairs first, then cosmetics. Easy and inexpensive to fix the railing(s). As for the stairs, I would go in this direction for cosmetic changes or really gray treads and white risers.

If you do replace the roof then that will definitely impact your other decisions. I don't think the white has "messed up" anything but I would stick with white trim. If you're interested in seeing full mock ups showing different shingle colors with painted, stained doors, etc., check out my web site, Creative Visual Concepts. I could show you different versions virtually that might help you make your decisions.

Nice little cottage. I would play up that aspect. Right now the entire house looks sort of washed out. I would paint the main body of the house a deeper color, blue, gray, etc., the windows white and take the railing down and beef up the columns. Then paint the door a bright color to draw the eye. Finish up with some landscaping and you're done. If you're interested in seeing some virtual makeovers of your home check out my website, Creative Visual Concepts.

Agree with the comments above. Your garage door needs to be changed - at least painted, but a wood or wood-look door would be better. The shutters are okay to me. They could be painted a darker color depending on your roof color. The biggest improvement you could make is the landscaping and the walkway to your front door. Here are a couple of insp pics below for you but the best thing for you is to post in the landscape subforum here to get an idea of what works for your specific home. Wide welcoming walkway in a material different from your driveway. Have the walkway come further down the driveway. Landscaping that isn't a series of bushes lined up against the front serving as a barricade to the house. I prefer a lighter or bolder accent color on your front door as it appears to be sunken into the shadows right now. As an added step you could tie in your front door color with the same color plants in strategic locations. Bring some color and life to your home with the plants and deeper planting beds. Frame your home with a tree or two. The landscape subforum will be able to help.