Mix the trim paint, and pour some into a clean bucket for "cutting in" with the brush instead of working out of the paint can. Pour some paint into a 5-gallon bucket for rolling. It's much easier to move a 5-gallon bucket and grid around outside than a paint rolling tray.
Cut in corners, grooves and angles with a 2 1/2- or 3-inch brush. If you are working two or more stories high, work in sections and roll each section after you have cut in. If your home is one story, it will be faster to cut in from the ladder, and roll the flat areas with an extension pole from the ground.
Roll eaves with a 9-inch roller. A 1/2-inch lambswool roller cover costs a little more than a synthetic one but holds more paint and gets paint into grooves and corners much more efficiently.
Use a smaller roller for trim. Rollers are available in sizes from 3 to 14 inches; a 6-inch roller is a versatile size for most exterior trim. Always paint edges and corners with the brush first and then roll.
Mask the body of the house using masking tape and paper. A hand-masker is an indispensible tool for this. It allows you to quickly and precisely apply masking materials. Use two bands of 9-inch masking paper, taping it along the bottom edge of the eaves.
Spray the eaves. Avoid the temptation to spray the fascia and gutters at the same time because you will get paint over spray on the roof, which is impossible to remove from most roofing materials. Paint the fascia and gutters after you spray the eaves.
Remove the masking paper and tape after the eaves are dry, which should take between one and three hours, depending on weather conditions. Save time by painting the fascia and gutters while you're already up on the ladder removing the masking materials.