Paint jobs will go relatively smoothly if you keep a couple of things in mind. First, surface preparation is critical. Second, don't skimp on quality. Top-quality paints and tools offer the best results.
If you're thinking about painting the exterior, get to it before the weather gets too warm and sticky, which affects drying. Windy days also are not good, because you want the paint to set up properly before it dries.
It's also best to avoid painting in direct sunshine, since the surface of your house can be 10 to 20 degrees hotter than the air temperature - and that can cause the paint to dry too quickly. By painting in moderate weather, you'll get the best performance from your paint and efforts.
Before you begin to paint, inside or out, make sure the surface is clean and free of chalk and dirt. Use soap and water with a scrub brush, then rinse.
Remove any loose, flaking or peeling paint by scraping, sanding or wire-brushing. (You might also consider wearing a mask and safety goggles.)
Feather back rough paint edges by sanding. If you are repainting a glossy surface, be sure to sand it, so the new paint will adhere better. And spot-prime any bare wood.
Finally, brush off any dust or particles left from the sanding and scraping prior to painting.
For durability, be sure to purchase the best paint you can.
For exterior applications, acrylic latex paint works very well. Its flexibility enables it to expand and contract with the surface when temperatures rise or fall dramatically.
That also extends the life of the paint job.