Turn oven to 350. Slice the neck portion away from the bulb portion. Peel the skin off of the neck section and remove the stem. Carefully chop into a small dice, about 1/4". Toss with some olive or sunflower oil, and spread out in an even layer on a baking sheet.
You can simultaneously bake the bulb section to have the extra cooked squash for another recipe, but you won't need it here. If baking alongside, scoop out the seeds and place cut side down in a small baking dish with about 2 inches of water. Place squash(es) in oven for 30-35 minutes, tossing every 10-15 to prevent burning.
Cook your bacon to be about medium crispy--can be done in oven alongside squash or in a high-sided skillet or griddle. Reserve bacon fat for another use, set aside bacon. Once it's cool, roughly chop into small pieces.
Chop your apple into a similar dice as the squash and allow to marinate in the lemon juice from 1 lemon.
Chop the cheese into the same size as the rest of the ingredients, about 1/4", and set aside.
Next stop, kale: if you're using a curly kale which is much tougher than a flat or lacinato type of kale, it needs to marinate in the dressing for longer-- up to overnight, but a few hours should be sufficient. Either using a knife or a food processor, finely julienne or shred the kale. Easiest way is to first remove the tough stems from the center (hold the tip of the stem with the leaf pointing down and slice the knife alongside the stem on each side, machete like removing the leaf.) Stack the leaves. If using lacinato or flat kale, roll it up to make a little burrito. Then, moving along the skinny way, thinly slice into ribbons.
Make the dressing. In a high sided bowl, add the apple cider vinegar, the lemon juice from 1 lemon, and the honey. A pinch of salt and pepper. Begin whisking, and then slowly start to drizzle in oil. Start with about 1/4 cup and taste it-- if the acid/lemon is too strong, add a bit more. If it's too creamy, splash in more vinegar.
Massage about 1-2 tbsp dressing into the kale. You can always add more dressing so start light. The fat and acid combo in the dressing breaks down the tough, fibrous quality to the leaves and makes it more digestible. You aren't going for a mash, just slightly softened. If the kale is still quite tough, let it marinate in the dressing in the fridge for a few hours.
Right before serving, toss with the bacon, cheddar, squash and apple. Add some salt and pepper, and serve!