Here's how I'd change it. Notice now your front entry becomes the focal point of the house? I also lowered the stonework on the areas where it meets the siding as it looked off dividing the house almost in half like that. I personally would also get rid of the arched window. It adds nothing and competes with the lines of the house. Here's how it looks without the arch.

Kay has a point. I think since you have the mahogany doors, I would just let them stand as they are. Paint the gable trim the same color as the siding that they are in front of. Stain the porch posts like the garage doors, and maybe the front door also, if you don't have it painted already, and call it good. With the Mahogany on the exterior only, it will give warmth and color to your landscape too, and your house.. Than let your Jacobean shine inside. Painting the trim in the eaves light gray, will be easier to maintain than staining so high off the ground in years to come. Your home will be lovely, and that way your Mahogany makes a statement at the entrances of the home, and it will make your home very special..

Thanks for the replies everyone!! I tend to agree with Izzy... I'd like to add a touch of colour to the gable. Nothing too dramatic. I like the dark trim though. Please take a look at these options and let me know which one you prefer! While the exterior colour is SW creamy, it leans a bit more gray than stark white (which I quite like actually). I tried to stick with soft greige colours Soft Sage Gable Intellectual Gray Gable Mindful Gray Gable Black Bean Gable (just for fun) Here's a bonus before picture... Really shows what a bit of paint, landscaping and TLC can do to a house!

Decoenthusiaste - thank you for the time you took to share your thoughts! The windows are a little difficult to decipher in the picture, but right around the white vinyl windows, the brick moulding is already wrapped in the off white aluminum. The was done when the windows were installed. The installer said he would just leave the window trim like that if it were his house, but he can build-out and wrap the rest of the window trim that's there (the greige color around the off-white on the windows), if we want. All the trim on the back and sides of the house (facia, soffit, window brick mould) is already done in the off-white color, so going forward, we are committed to that color. I understand what you are saying about the vertical trim, but I sort of feel like some vertical contrast helps keep the house from feeling so heavy and weighed down since the the house is so roof heavy. At least from the front view. Would eliminating the inside corner, vertical trim, help some? My husband would kill me if I suggested painting the downspouts! They were installed when we had the first side of siding installed, so they are newer. He is all about "maintenance free" hence the steel siding choice. We chose the color because they match the off-white trim color and the downspouts are all pretty much over a trim piece/corner, so it made sense. We do need a new door. Do you have a style suggestion? Do you think the top middle gable has enough room for a faux gable vent, with those small windows right below it? The porch is weird. We agree. It had a white rotting fence around it when we moved in. We sort of just ignore it for now. I'm not sure much can be done about it at this point without significant work/expense.