I would suggest when you do paint the house that you paint the whole house first with that strip painted out so he can see it without and paint that piece of the trim last as then you can see how it would look without and with it. Well what I was trying to say is your house does lean towards the spanish revival and you keep saying you want spanish and not tuscan, mexican etc. and really what is spanish color theme tends to be white or a very light color that reads white with a darker trim color such as brown, or more very muted colors. Landscaping makes a huge difference in how a house looks too. What I'm wondering is if you really have settled in your mind what you want the house to be or if you really need the house to be one particular style. Many color will work for your house as long as you pick something that works with the roof color. Maybe it is your mentioning spanish that throws me off. BTW if you look at the picture I posted it is a very simple style except for the tower and the other items are things your house has or will have too. You have arches, you have the curved wall, the raised trim, you're adding a pergola (not a porch like in the house shown). You could on your gable sides add corbels either dark stained wood or faux looking wood like you're planning for the garage door. If you look at a spanish villa - they tend to be white, with tile roofs, mainly boxy. Some have arches, some have railings that are often white and look like concrete formed (don't know the correct terminology). I guess I would ask yourself do you want the spanish look, or does it really matter and should you just go with a color that you like and not worry about trying to keep to a particular style?

I feel like the railing on the steps is not the right size and sticks out. Maybe replace with a black wrought iron railing that is more subtle. Trim out some of the overgrown shrubberies. If you can forgo the storm door, remove it. Paint the front door a bright color.

I would go more mid century modern. Dark gutters and roof. Leave the brick as is and leave the eaves white. Modern light fixtures and landscaping. Remove the landscape timbers on the left so you can see the brick ledges under the windows. Remove the bench and pop the front door with an orange color. Check out mid century modern homes on Houzz or Google.

Everybody has an opinion, which you asked for, but you have to do what is best for you in your neighborhood. If you are replacing the siding and thinking about doing all the work of painting brick, maybe you should just remove some of that brick altogether. If you leave some of it, have it be lower and even across...maybe 1/3 of the height of the walls instead of half. Keep the excess brick for edging or patio like someone else suggested. I liked the trim-work you added. Definitely do not paint the garage door the same as the front. Keep it in the lighter tone of your siding color choice. This way the front door is a focal point. Do not replace the garage door if it is not needed. There's no reason to add the expense ($1700 or more). I would use the existing shrubs as background to a much larger planted area. Allow budget for mulching that planting bed and, for what it's worth, consider using rubber bark mulch. It definitely is more expensive, but it is worth it in the long run if you're planning on living there. Rubber bark does not attract termites or roaches, it doesn't fade, it doesn't disintegrate, and it doesn't blow away so it doesn't need to be replaced every 2 years like bark mulch. It keeps tires out of the landfill! Anyway, updating is a great idea, but keep in mind why you are choosing to do so. If you are going to live there, spend what you want. If you are updating to sell, keep your budget as low as possible because you won't recoup much of it and expenses can only be subtracted from profits on the house. If you're losing money on the house then not even the realtor fees are deductible. Best of luck with your project!