OK, what is your hoped for budget, because this is a big wish list. New windows (don't know how many but figure at least $300 each for materials, you can remove the shutters, they do nothing for this home. A porch of the size in your dream photos, means new footings, architect to design structure so it is proper and fits the house, materials, labor, depending on how complex the design, at least $20K. Probably more if you keep true to proper design of the house and don't just "tack it on". Siding another $4-6K -- it goes on. I am not sure this much work would be supported by the comps in your area? I would consult with a real estate agent familiar with the area and see what they say. You will probably also need a new front door. It adds up for sure.

I like your house! I love the idea of doing a large porch overhang (like your second and third pics), siding it all with LP (including the brick area), but I think the dollar amount to do that could climb high pretty quickly. Do you think you would regularly use the porch, or would it be more for curb appeal?

Thanks for the thoughts! Yes, we know this is going to be a pricey update. I do believe we could get our money's worth as our neighborhood has a variety of price points (many higher than ours) in a desirable neighborhood.

Any thoughts on a color of siding that would look nice with our roof? We'd like to get away from the current tan color. The outdated brick is throwing me off. If we eliminate the brick, I know that opens up so many color options for siding. If we have to keep it, I'm at a loss!

The porch is simply a dream of mine. I have no idea how much it costs, but would love to look into the potential.