Vertical Siding & "T111" Plywood

Starting at the top

Generally paint your house working from the top down, but following the run of the boards. Prime the overhangs and fascia boards first.
At the eaves: start at a corner, paint the overhang all the way across before starting the siding. From this point you can move onto the siding. With vertical siding; work from the top of a board to the bottom. Set your ladder about 20 inches from the corner of the side (Right side if your right handed, Left side if your left handed) and so that the top of the ladder is about 2 feet below the overhang. Start a strip of boards 14-20 inches wide. (With T111 use the groves as a guide still taking a strip 14-20 inches wide)  Work your way down, working to one side of your ladder, lowering your ladder as needed until you get to the bottom, or a good stopping point such as a casing or an overlap joint. You can leave off for a break whenever you get to the end of a strip or a casing board. As you finish the strip, move your ladder over and paint the next adjoining strip. When you reach the last strip you will have to work above the top of you ladder, so paint about 2 feet down then lower the ladder and paint another 2 feet down until you reach the bottom.
At gable ends: Start at an upper wall corner, paint the overhang working your way up toward the peak up, and then work from the peak down to the other upper wall corner.
From there you may move onto the vertical siding. Start at an upper corner follow the same basic procedures as described for at the eaves above, however you will be raising your ladder each time you move over to the next strip until you reach the peak, then you will be lowering the ladder each time you move.
Window casings can sometimes be reach entirely from having the ladder set on or under the windowsill of shorter windows, however tall window casings will have to be painted with your ladder to the side of the casing.

Applying Finish Paint
The methods for applying the finish coats are basically the same as we have given for applying the primer. During most of the painting season you will want to avoid painting on the sunny side of a building, so rotating to a different side before one side is finished is usually necessary. Some paints are ready to use directly from the paint can, while others perform better for us if we thin them slightly. While painting, you may find it necessary to thin paint, as it sometimes tends to thicken up in your paint-pot (Bucket You Work From) during the day. Be careful not to over thin.

Drying Time

Read paint can labels for recommended times between recoat.
Not to soon: Latex paint may have a recommended recoat time of less that 2 to up to 24 hours, however cool damp or humid conditions can slow drying time significantly. Oil/Alkyd paints usually recommend at least an overnight dry between recoats, however we have found that with some finish coats; it is better to allow the paint an extra day dry time. If oil/alkyd paint is recoated to soon, it could possibly wrinkle, and this is a situation you defiantly want to avoid.
Not to late: Some products are known to produce a soap like film in time thus, possibly affecting the adhesion of following coats. In this case you will probably be advised to recoat before two weeks. Glossy finish paints tend to harden over time, and this could create a surface to hard and slick for the following coat to develop a good bond with.
Letting the paint dry for longer than two weeks before recoating will often, not create a serious bonding problem. But if you ever see a house, that has a problem of paint peeling from paint, it could have been cause by to much time between recoats, if not something else.

Multi Colors

If you are using more than one color, let the first color paint dry before cutting in with the next. Paint overhangs first. Other trims colors can be applied before or after the siding is painted. If the edges of casing boards are to be painted along with the siding paint/color, and the face of the casing boards are to be painted with a different paint/color; than it will be easier to paint the trim after the siding is finished.
It is usually best to finish the doors after the siding is painted.
 If window sash is to be painted, it can painted before or after the siding is finished. By getting the window sash done before the siding is finished it prevents you from placing a ladder on your freshly painted surfaces.