So, all of your watering systems are in the run, and not in your coop? How do you set up electric to be weather proof? Does your 250W deicer have a built in thermostat?
In my smaller coop (4 x 8) the first year with 5 birds, I gave them a flower pot heater for those days on end that never got up to 0*F. It may have raised the temp a few degrees, and they could have snuggled up to it if they wanted. Last winter, in 10 x 12, I gave a bit of heat, at night when they were hypothermic. (depressed appetite, as well as decreased activity level: standing around with feathers fluffed all day) In your smaller coop, you will need to be sure that they have plenty of ventilation which is not at comb level. Also, be sure that when they roost, that they are not too close to the wall. If their faces are close to the wall when roosting, their exhaled moisture condenses and produces a perfect set up for frost bite when they are close to the wall. You'll also need to be sure that when they are on the roost that their feet can be flat, not curled around a skinny roost pole. 2 x 4 laid on the flat is good. Do they have a run that they can access in the winter? "They say" that chickens DON'T need heat in the winter. For the most part, I'm inclined to agree. But, when I see my flock eating LESS, and not moving well, IMO, they are NOT doing fine, and will benefit from a few degrees of heat. Katelyn, have you been to the Maine thread? You might want to join us over there. Also, are you going into the winter with a flock as big as you'd like? An extra body or two might help, but you would also be dealing with introducing birds as they are moving into the most stressfull time of the year. It would depend on your set up, and if you have a run that is sheltered enough that they will use it in the winter. I have been using a 5 qt heated dog bowl with a gallon jug of water set in the middle for my smaller flock. Need to upgrade for larger flock this year.
I have 3 "larger" coops (8x12 hoop, 14x16 hoop, and a 10x12 old loafing shed style plywood coop). IN two of these I have a 65 gallon rainbarrel set up on a 30" stand, and the water is heated with a thermostatically controlled 250 watt API bucket heater. The wood coop has a GFCI safety outlet and all the water heaters (3 total) are run from a heavy duty (12 gauge) extension cord. The cord connections to the heaters are secured with a "cord connection protector" which is supposed to be water safe, and these make the connections chicken-proof, as well. I mount the cords so that the connections stay OFF the floor. I have waterers with horizontal nipples both inside (one is right beneath the spigot of the rain barrel) the coop and outside the coop. The outside waterer is a 20 gallon plastic trash can set on a stand OUTSIDE the run. It has a horizontal nipple and supplies water through the wire run enclosure to two cocks separated from the flock in the coop. The water is heated with a deicer on a heavy extension cord run through a notch in the closed pop door to the the outlet in the coop.
My other two rainbarrel heaters are run from heavy duty extension cords plugged into GFCI circuits, on the patio and in my shop. One of these is on a stand central to a number of smaller hoop coops supplied with their own heated bucket waterers or flip latch totes. When their waterers need filling, I run a hose from the water barrel spigot to the buckets. The buckets are OUTSIDE the pens, and the chickens have to come out of their little shelters to access the nipples through the fence. This set up will not work well on level terrain, as the water delivery is gravity fed. A small utility pump might work, though.
Most of the cord connections are done with "water proof" connect-locks, and the connections are hung on the fence, off the ground. I have used another type of home made "water safe" connection employing a multi outlet extension inside a bucket, lidded and wrapped in a plastic bag. The Internet net has a number of videos on how to make water proof connections, and it's a good idea to research them.
Electrical is a rather specialized field, and not being an EE, I have trouble making recommendations. Before I started using bucket heaters, I made the light bulb in a cinder block thing, which also works well; it's cheap, doesn't use a lot of electricity, is easy to make, and lasts a long time. If you use white buckets, they light up the night with whatever color bulb you put in, and it looks like a holiday. And you can see immediately if your heater is on or needs a new bulb, or has come unplugged. If you use these with Thermocubes, your water will not over heat.
It got really cold last winter, and some of my Roos' combs got rather severely frost bitten. I used "huddle" boxes in small shelters, and instead of keeping to their small groups, my different groups of birds all piled in together in one box. Just as one large shelter may not keep too few birds warm, a small enclosure may make too many birds too warm and moist. This box that everyone piled into could be seen steaming, and snow never stuck to it, even though it had a lot of ventilation. Warm and moist, and when they came out, their combs froze. Word to the wise: match the coop size to the number of birds.
Yes, my birds are starting to look a little unhappy, and they are staying in the coop. Some don't seem to mind the snow and the cold at all, but I think my daily visit actually cheers them up, especially when I bring them scrambled eggs and scratch soaked in milk. I think they forget to eat when I don't visit. Even/especially as chicks, they would start eating the moment they saw me.
This was lengthy and I apologize. I should have taken pictures. Hope I answered some of your questions.