IMO painting the siding is where is where I would start.What look are you wanting ? Are those copper roofs over those windows ?Do you need a new roof? if you do then IMO you figure how you want the house to look then choose a roof color. I would lose the angled corners on the garage openings and get garage doors with glass in them too

Thanks so much for your thoughts! I don't love the siding or color but it is in good condition and does not need to be replaced so prefer to work around it. We don't like the existing brown color palette and want the house to look more current but still fits the colonial style. Yes those are copper roofs over the windows which are very faded and I assume need to be painted. The roof does need to be replaced so can go with gray or black singles once we decide the other color choices.

Don't paint the copper roof! The patina is beautiful. I'd take inspiration from that and use a slightly deeper blue/green for the front doors and shutters. Paint the garage to match the siding, or white to match your trim.

Agree with calidesign but I would replace the front door altogether with something colonial, not Victorian.