I LOVE your house and II would not touch that mortar - it goes nicely with the aged stone look. I would stay in the brown family for roof color to compliment the aged stone look - not a color that is bright or harsh or crisp. The door is too "fancy" for the house and all the trim is too "crisp" white...look in the cream/taupe/earth-tone family. Not navy or black. Shrubs need to go - think subtle English countryside landscaping. I also agree on clapboard, not stucco, for your addition. I can see ivy climbing the walls - but won't suggest that as you can never get rid of it and it is not good for your stone. Looking forward to your transformation.

Many options, Look through Houzz for ideas and post some of your favorites! Best wishes!

you already have the dark windows, so that's good. do a medium gray roof. that color will go w/everything. Do you like dark? if you did the dark siding and added some wood composite siding, it could look a bit more modern. I notice you have some cedar up under the roof eaves. that would be cool if you could do it elsewhere on the home. similar home style with a darker green siding and the brick lighter gray (btw, these all have the stairs like you have. check out some of the landscaping around them wood doors, and all the siding running the same way. Another gray with shingle siding. arbor over garage. cool landscaping here's a before and after where they painted the brick and did the black windows and added some wood siding accents

I like your third combination but think the Intellectual Gray from Marylee might be better for the siding. Is your tan roof more warm or cool? Another option might be Intellectual Gray with white trim and shiny black door.