I would keep the roof that you already have over the porch. It fits the house and blends with the existing roof lines. I think, the house looks nice already with its windows and the color. I wouldnt be changing anything there, except another coat of paint, if it really needs painting. Put your money into landscaping, which you really need. It would be a good idea to go see a landscaping company, and have them draw up a plan. If you intend to do the planting yourself, you can follow the plan, they draw up for you, otherwise, they will do the planting for you too. The landscaping you have is not great, and should be all replaced, and extended out a bit further, and not all in a straight line against the house.

Hire an architect to help you visualize what is possible.

IMO remove th e shtters apint all the white a soft gray green and work on landscaping , done and a hyge improvement IMO . This will never be either style you want

You have a fine house. It is not going to be Craftsman or Modern Farmhouse. Consult a structural engineer about moving the columns.

Professional landscaping could turn heads once the new plants get settled in. This is a good time to plant bulbs for spring while you consider your plans for changes over the winter.

I like the shutters on your house. They do add interest, so I would leave them. I agree, get structural eningeer to move the columns and I see in your pictures, why you want them moved a bit.

Whats behind the siding, I dont think it is OG to the house. Looks also like at some point a smaller window was put in and that siding was added. Unless the windows are bad they dont need to be replaced. I would dump the money into new siding and landscape.

Something about your house reminds me of a Garrison colonial style. Even thought it doesn't have a projecting second story, it's a visually prominent second story because of the overhang and high contrast between siding and brick. You might look at some pics of Garrison colonial renovations to get ideas.

It is an attractive house, doesn't need structural changes IMO but would really shine with better landscaping. Big shrubs and small trees, no small boxwoods or little flower beds. Would look great with some of the 12 foot Limelight hydrangeas that are in bloom now.

Not exactly like yours, but might be a good inspiration pic if it's similar to the look you're going for.

Do you really need new siding and windows? Houses are built to last, not to have major elements replaced when the trendy winds blow a new direction.

Some inspro

No to black windows for that house. as they will look like black holes. Lose the front double door, get a single with sidelites. Absolutely a big no to shutters.

If I were doing a makeover on this house, I would consider something like this.

Plenty of details to work out, so see this as a concept.

I'm not suggesting these colors, just showing how making the 2nd floor darker helps it recede.

Are you after this kind of trend?

yes @Kendrah somwthing like that

With the red brick I would look at Dark Bronze rather than black. The windows will not be so stark and black hole appearing and the bronze will blend much better with the brick.