What a fantastic architecture. When you do the brick, if you stain it with masonry /concrete stain you won't have the same issues of maintenance as with paint. They will spray it evenly - through you will have to select a deeper color - either taupe (brown-gray) or a straight charcoal. Love your windows and the classic angled railing. I think a dark gray on the siding will make the orange brick jump even more. What bothers me is the white (railing, fascia, eaves) juxtaposed with the earth toned stuff. So I would recommend camel tones - for the siding - something like http://www.sherwin-williams.com/homeowners/color/find-and-explore-colors/paint-colors-by-family/SW6108-latte/ and the hopsack next darker tone for the garage door. Use the lighter tan for trim that is now white - http://www.sherwin-williams.com/homeowners/color/find-and-explore-colors/paint-colors-by-family/SW6107-nomadic-desert/ Use the darkest tone if you are painting concrete steps. If you think you will stain your brick charcoal, then the white eaves and trim are probably right, and you may not want to paint it tan now and then go back. If your brick were charcoal, then I would block out the rest in grays and blue grays - leave the white eaves, but take the railing and posts charcoal too. A blue gray door - like sw smoky blue.

When you say "Do we paint the paneling as well as the other side - the rails etc." what exactly do you mean by 'the other side"? Are you referring to the underside of the stairwell? If so, I would leave that element. If you paint the panelling just be sure to give it a sanding before doing anything. I just had the wood trim in my place painted (just baseboards, not panelling like this) and I was told that it didn't need to be sanded first. Boy, do I regret it - there are spots that are flaking off already, and it was a good quality paint and primer used. In your case, I would paint the panelling but not the banister and stair rails unless you are also planing on painting all of the wood trim upstairs. Doing the panelling will leave you with the lighter, fresher look, while still looking classic with the wood stair rails. Also, it looks like you have the wood panelling in the hallway/entry way leading to the stairs - I think you need to have a consistent treatment for both areas so would paint this as well.

It depends on the species of wood (I.e. How hard or soft) and whether or not the ambient temperature can remain as stable as possible. What you caulk and paint in warmer weather may look great now, but when it begins to get colder, the wood begins to shrink, and the caulk will begin to pull away. This will look worse than if you didn't caulk at all. My suggestion is to use a caulk like the brand called "Big Stretch " in an attempt to avoid this.

Okay, so I like it simple and modern, big stripes, big blocks, love this and this I really like uncluttered look. like this to https://www.houzz.com/photos/murphy-beds-modern-rendering-phvw-vp~24435627 , and I like my dark grey's and browns not to mention light blues, yellows, oranges and reds clashy aye.(not sure if these colors will work with the wood, really like the idea of staining the wood darker to more like this https://www.houzz.com/photos/rubin-residence-contemporary-bedroom-san-francisco-phvw-vp~5202610). But really interested in your ideas.