Step 1:
Estimate the amount of paint you'll need. Its better to buy to little than to much, you can always go back to the store and get more if you run out. Each brand of paint should explain how much it will cover.
Step 2:
Purchase high quality paint. You generally get what you pay for - its better to get good paint you know will last a long time than some cheap paint that's going to peel in a couple years.
Step 3:
Get good, sturdy ladders. (You'll be on them a lot). Make sure they're tall enough - you don't want to be standing on the highest step with a bucket of paint.
Step 4:
Purchase good brushes and rollers; ones used for exteriors are generally less delicately built and shaped than those used for interior of a house.
Step 5:
Purchase plenty of sandpaper, scrapers, exterior-grade putty, and exterior-grade caulk.
Step 6:
Buy a lot of masking tape and drop cloths to protect walkways, driveways and your neighbor's property. Cover your driveway its better to be safe than sorry. (I once dropped a bucket of paint onto my now ex-wife's driveway)
Step 7:
Consider using alkyd (such as oil-based) paint for exterior woodwork. It dries slowly and is a little harder to use, but it's also a lot tougher. Use it especially on areas that get a lot of wear, such as doors and their trim, banisters, and porches.
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