Picking exterior house paint colors is a lot different than picking a color for a shirt or a car.  It may help to drive around to observe colors that other homeowners have combined on homes that are of similar size and design as yours.  There are also online resources that provide homeowners with the ability to create virtual makeovers of their home by combining colors together through their software programs as well.
If less than half the old paint is left, however, it may be worth stripping it all off. Guertin gets rid of stubborn remnants using shrouded grinders (like the PaintShaver), infrared paint strippers (such as the Speedheater), or chemical strippers (like Multi-Strip), then smooths the wood with a course or two of sanding. When siding (or bank accounts) can't take the shock of a total strip job, Rich O'Neil, of Masterwork Painting in Bedford, Massachusetts, has successfully hidden rough, well-adhered paint under Peel Bond, a thick primer. Denver House Painting
O'Neil patches shallow holes and divots with Ready Patch because it dries fast, sands smooth, and stays flexible. Deep cracks and rotten spots are best repaired with two-step epoxies, such as those made by Advanced Repair Technology. (For a step-by-step instructions, see Repairing Rot with Epoxy.) The days of using polyester auto-body fillers on wood are over. "They cure too hard," says Portland, Oregon–based painting contractor Kathleen George. "They look good at first, but then they peel away." House Painting

The last big decision is how to apply the paint. Most pros use paint sprayers because they're fast, but in inexperienced hands a high-powered sprayer can leave drips, thin coats, and a mist that may land on many things other than your siding. If you do hire a painter who uses a sprayer, make sure he is meticulous about removing, covering, or masking off everything in the area that might get hit with overspray: gutters, roofs, windows, shrubbery, walkways, cars—you name it. Denver Home Painting
You might pay an additional $1 to $5 per square foot for optional repairs and updates. Consider having your molding, trim and baseboards checked while you have a professional in your home. This might be a good time to upgrade or repair any cracks, warps or other issues. Pros can usually touch up or replace these items for an affordable rate, and they may even package such fixups with your project. House Painting
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