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Yes, you must use an extension cord specifically rated for outdoor use to power outdoor lights, such as Christmas lights. Extension cords intended for indoor use lack the protective properties to withstand exposure to outdoor elements. To safely hang and power lights outside your house or in your yard, always connect them to an outdoor power source using an outdoor-rated extension cord.

How many string lights can be on one outlet depends on a number of varying factors, including the total wattage of your circuit, the type of lights, the energy needs of the lights, and cord specifications. It’s better to play it safe here to protect your circuit, so figure out the max wattage of your circuit, compare that to the lights, and move on from there. Generally speaking, LED string lights require less energy than incandescent bulbs, translating to a higher number of lights per circuit. 

You should always hang the lights before the ornaments because hanging lights on top of ornaments can cause some to fall off. If a light sits directly on top of an ornament, it can cause it to heat up and possibly change its color or cause it to crack. 

Ensure you have a safe environment for them to work on, and there aren’t items such as logs, build-up of yard materials, missing or damaged shingles, and weak areas on the roof. Communicate any known electrical issues with contractors at the beginning of the project, and consider hiring an electrician to fix those. Finally, if you are attempting the project yourself, do so when there isn’t any rain, and you can safely get your footing on the roof using proper equipment, such as an extension ladder. Don’t attempt this alone, and have a helper nearby to assist.