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It's safe to hang Christmas lights from gutters with a few considerations. First, when installing the lights, follow safe ladder-use guidelines and avoid getting onto the roof. Second, for best results and the integrity of your lights, use clips to keep the bulbs away from inside the gutters where they could run into trouble with water or ice. 

Nails are a popular choice for hanging string lights, but they are not the only option. Use outdoor hooks, zip ties, or even awning hangers to string up lights outdoors. For indoor lights, use simple tacks, zip ties, damage-free adhesive hooks, or drawing pins. When all else fails, just wrap the lights around some furniture or outdoor fixtures. 

Inspect for burnt-out bulbs, secure connections, and protect from water exposure to maintain functionality.

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.