I think I would also be like you and need to paint while the house is empty. I think the suggestions above are good ones. Also look at Revere Pewter, a Ben. Moore color that is very popular. It's a warm grey and you can do a search and find it here. Also, a neighbor of mine just painted her living room and hall a color called Dune Drift in the Seaside Collection by Valspar paint, sold at Lowes. It's a very calming color that is a neutral greyed green. A great Ben. Moore color that a few friends used and I love (and wish I used it in hindsight) is called Bamboo Shoot #1529. The other colors on the same strip as this that are deeper in color are also beautiful (Ocean Pebbles). My daughter just painted her bedroom BM Coventry Grey,a beautiful grey (cooler grey with a trace of blue). She says she feels like she is living in Nantucket. Beautiful with white molding. I have seen photos of most of these colors on this site. I don't like how the colors show on My Perfect Color, so don't check them out there. Sorry, I don't know any specific colors by Behr, but they will match anything because the color formulas are in their computer.

I think a light grey would look very smart - white trim. Be sure to paint the garage door the same color as the house to help it disappear.

I'm cracking up because of the number of colors you have tried. I'm the same way when it comes to finding the perfect option for just about anything. Maybe you are simply looking to have fun with color and want more than two colors on your house, but I like to make gutters as inconspicuous as possible. So, I would probably paint the fascia the same color as the window trim and gutters and the soffit either the same color as the house or the same color as the fascia. The sandy accent color is nice, though. If you don't mind the gutter being more noticeable (or change them to match the fascia color), you could paint the fascia Ponytail and the soffit Navajo Red.

Keep the shakes! They lend your house character and texture and are fitting for the style. I think it would be bland without them. However, that doesn't necessarily mean you need to keep them stained. Paint is always an option. White is always a classic choice and never goes out of style, whether you keep the shingles stained or not. Greys have been around for some time now and may begin to look dated sooner than you'd like. One idea that I have been loving a LOT is to go darker. Just an idea! Best of luck!