http://www.diydata.com/techniques/stucco/stucco.php

I LOVE the character and warmth of weatherboard homes, so personally I would re-clad in weatherboard, you'll be amazed at the difference it makes to your home and weatherboard would work beautifully with your gorgeous windows. Just make sure you have addressed whatever caused the water damage in the first place - rising damp, leaking gutters etc.

Hi Amanda, tricky... I would suggest rendering the brick and the upstairs exterior so it all hangs together. Use a poly-render. The upstairs currently looks like an after thought and is not working with the rest of the building as it is. I would paint the render and roof in colours that work with your existing front door and windows as painting these is not a long term option that is going to last without a lot of maintenance. So I suggest using the existing roller door colour for the exterior walls with a heritage red roof, gutters and downpipes. Above all keep it simple.

I personally love the look of a Tudor style home but if you are looking for a more modernized american look I would suggest removing the trims and painting the entire house white. If your budget allows for re-cladding the roof or painting the existing cladding (maybe in a black or charcoal) that would help to modernize it as well. it would also give a dramatic contrast with the white and then add some navy or black shutters as well.