If your house has gable ends, you can estimate by just adding 2 feet to the height when making your calculations. If you will use a different paint on your home’s trim, subtract 21 square feet for every door and 15 square feet for each typical window.

To convert this number into gallons of paint, divide the square footage figure by the square-foot coverage specified on the paint can’s product labeling.

If you are using a custom-colored paint, it might be a good idea to buy and extra gallon for insurance.

There are two things you must do first. One, check the long-term weather forecast. Refrain from painting when the temperature will below 50 °F. Also avoid painting in threatening weather – a rain shower can ruin a fresh coat of paint.

Two, take some time to be thorough with taping and drop clothes. This extra precautionary step will pay off in the end. It will result in a more professional-looking paint job and far less time spent cleaning dried paint off of places where it shouldn’t have a landed (a loathsome task).

Use masking tape specifically designed for painting. This is especially important if the tape will remain in place for more than a few days (and likely baking in the sun) or if you’re taping the glass on wood windows. Use the tape to protect any small items adjoined to the siding; cable boxes, meters, light fixtures, etc.

Place drop cloths on any surface that is directly below where you’ll be painting. Large, professional-grade canvas drop cloths will prevent any paint from leaking through them. Use these on critical surfaces like driveways, sidewalks and decks. Areas like bushes and drain pipes can be covered with old bed sheets, blankets, or tarps.  Paint will bleed through those materials, so make sure to only use them on less-critical areas. NEVER set an extension ladder on a plastic drop cloth because the feet might slip. This could lead to serious injury and even death.

Overall, try to have enough drop cloths on hand to completely protect at least one side of your house.

In most cases, you will want to paint the siding on your house first and then paint the trim. An exception to this would be if your house has wide overhangs or soffits. These should be painted first in order to prevent splatters on your newly painted surfaces.

You’ll want to begin painting on a side of the house that is in the shade. Once you’ve chosen your side, you know where to set up your ladders. Before placing your ladder against the house, put ladder mitts on the end of the rails to protect the siding from smudges and scratches.

There are a few key tools that you will want readily accessible when you are up on a ladder painting. Loop a damp rack through a belt loop and stick your painter’s tool in your pocket in case you discover any peeling paint that was missed previously.

Focus on the upper leftmost point on the side of the house. When loading your brush with paint, immerse the first 1/3 of the bristles into the paint and lightly tap the brush side-to-side against the inside of your paint pot. Do not drag the bristles across the lip of the pot; this will rob your brush of half of its paint carrying capacity.

Brush out the fascia boards first, then work on the underside of the eaves. Oil-based house paints should be brushed back and forth several times for a well spread, even coat. Usually, there are joints between the sections of the eaves; do only one section at a time to reduce the chance of the paint flashing.

Once these trim areas have been taken care of, you’re ready to move on to the siding on the same side of the house. Pour your trim paint back into the can and tightly seal its lid. Wrap your brush in plastic to keep the paint from hardening.

Open each of the gallons of paint that you bought and empty its contents into a 5-gallon pail.  Then put a power-drive paint mixer into your trusty drill and mix the paint thoroughly. It’s important to always stir paint before and during use. Make sure all the paint is combined to ensure a single, uniform color. Once the paint is completely mixed, you’ll want to leave the 5-gallon pail half full. Pour any leftover paint back into their original cans and seal them tightly.  The half full 5-gallon pail will go up the ladder with you and hang on a bucket hook.

The techniques you will use for painting siding will differ depending on whether your house has clapboard siding, plywood siding, shake siding or masonry type siding.

Clapboard Siding
To paint clapboard siding, once again focus on the upper-left section of the side you’re painting. Plan to do 3 to 4 boards at a time and set the ladder just under the last coarse of siding that you intend to paint. Work from side to side beginning at the top, reaching as far as you can safely on this section.

One of the main causes of bad paint jobs is the painter not using enough paint. Lay the paint on liberally.  Start by painting a sharp line between the top board and the trim as far as you can reach. Then coat the lap joints between the remaining boards in the run.  Finally, brush the faces of the boards and smooth out the paint.

TIP: Before dismounting and moving the ladder, check your work for drips, runs, thin areas and missed spots.

Then come down off of the ladder, bringing your paint pal with you  Keeping the ladder at the same height, move across the house to do the next section of clapboards before the paint you just finished applying can dry. Climb back up the ladder and start by brushing from the farthest point, back into the first section of wet paint. Keeping a wet edge ensures that you won’t end up with lap marks. Work across the house like this until you reach the next corner to complete the run.

Then lower your ladder, move back to your starting point and paint another few boards across the house.

Plywood Siding
Though not nearly as common as clapboard siding, there are still some houses that have plywood siding. Among them, T-111 is probably the most common. To paint plywood siding, work on a manageable 3 or 4 foot swath at a time. Work from the top to the bottom of the house before moving on to the next swath.

Roll the finish coat paint on with a thick roller and then brush it into the grooves if necessary to get good coverage. When using a roller, dip it into your 5-gallon bucket and roll it up and down on the grid to remove excess paint. If the roller drips paint when you pick it up, it is overloaded.

A roller is ideal for flat surfaces but will not fit into inside corners and will deposit too much paint on the edges of outer corners. Apply paint to those areas with brush but cutting in. Use long even strokes and roll in different directions to coat the entire surface. Finish off with strokes in direction.

Shake Siding
Shake siding has deep, uniform grooves running up and down. This type of siding can be painted using a thick roller.

However, sometimes paint can actually bridge the gap between grooves and dry that way. When this happens, it doesn’t adhere to the deep, inner part of the groove like it should.

One way to prevent this from happening is to roll the paint on the shakes with a thick nap roller, then go over the shakes with a 9-inch paint pad on a pole. By running the pad down the siding with a bit of force, you can work that paint into those narrow, deep grooves. Make sure to buy extra pads because this tears them up rather quickly.

Masonry Siding
Stucco and brick homes are the most forgiving type to paint. The direction that you run your roller or feather out your brush strokes almost doesn’t matter. Just make sure that you used a thick roller (preferably 1-1/4″) and put on a good amount of paint.

Stucco especially really soaks up paint. For best adhesion, brush in the paint with a wide nylon bristle brush. As long as you don’t leave obvious thick lines when rolling, it should come out looking fine.

Let the first coat of paint dry and add one or more additional coats, using the same rolling method. Two or more light coats are better than one heavy coat of paint.

Make sure that the siding is COMPLETELY dry before leaning a ladder against it to do the trim. As before, make sure that your ladder rails that will be resting against the siding have ladder mitts on them to prevent damage to the new paint.

If you’re not painting any windows, use a combination of a 3-1/2″ angled brush and a 4-inch roller (3/4 nap) to brush and roll your way around the house. When painting exterior trim, work from the top down; gables, dormers, crown mouldings, second-story windows, first-story windows, porches and stairs, then foundations.

Start with the highest trim pieces. At the top of your siding, there will usually be a top moulding of some type. Use the same horizontal painting technique that you did for clapboard siding. At the corners, painting the mouldings and corner boards down the ground before moving on.

Then move down to the next piece of trim, usually second story windows. Painting windows follows a logical process, working from the top, innermost parts to the outer, larger sections. Again, the innermost piece of paintable material will be much farther out on vinyl, aluminum or fiberglass clad windows than they will be on wooden windows.

If you accidentally over-brush or splatter and need to remove paint from the window glass, use a single-edged razor blade to scrape it off AFTER the paint has dried. Follow the same procedure on your first-floor windows.