I don't know why this picture is sideways. Trying to figure out how to fix it

Thank you! We're looking to make some big changes inside and out. The right side of the house is the garage, not sure we could extend the porch all the way to the right w/o tearing apart the garage? That was the one thing we weren't planning on touching, except maybe adding a master bedroom on top of the garage.

The house, along with its verdant yard and beautiful tree, is already quite attractive. I'd focus on adding whatever different or additional function or feature you need, and just design it well, so the character comes along for free. Porches are great if you really will sit out there and use them, but not so much if they're just dead space, or worse yet, the whole family's favorite place to stow sports gear, boots, dead plants, tools, and boxes.

Consider a kind of garrison colonial.