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Norfolk Island Pines can only tolerate temperatures down to 30F. If you get weather colder than this, it will not be able to survive year round outside. They do make great houseplants though. This article can help you with caring for them indoors:
https://www.gardeningknowhow.com/houseplants/norfolk-pine/norfolk-island-pine-care.htm

You can grow it indoors and this article will help you with that: https://www.gardeningknowhow.com/houseplants/norfolk-pine/norfolk-island-pine-care.htm

They are only cold hardy down to 25F. If it colder than that where you live, it will not survive outside. But, if it stays warmer than that, you can transplant it outside without a problem.

Yes, you can, but just to let you know, the older a plant is the more susceptible it is to transplant shock. This article will help with avoiding that:
https://www.gardeningknowhow.com/plant-problems/environmental/learn-how-to-avoid-and-repair-transplant-shock-in-plants.htm

Antime you repot, you should only go up another couple inches in pot size, so that may be a rather large pot. You should also make certain that whatever container you choose has adequate drainge holes. Simply placing pebbles in the bottom will not prevent root rot. Since you already have this pot, you can always get another smaller one, preferably a 24-inch (up 2 inches from the original) with drainage holes, and place it inside the other container. For tips on how to repot or how to care for this tree, these articles should help: https://www.gardeningknowhow.com/houseplants/hpgen/learn-more-about-repotting-houseplants.htm
https://www.gardeningknowhow.com/houseplants/norfolk-pine/norfolk-island-pine-care.htm

Hi. First of all, you should be real careful putting indoor potted plants outside - oddly enough, they can get terrible sunburns. Just like people who have never been out in the sun, their "skin" has no protection. If you put them out, they should be heavily shaded by trees, etc. That could be the cause of your NIP's leaf drop. Or, it could have severely dried out - it uses a lot more water outside. That being said, Norfolk Island Pines don't like to be cut back. You can try it of course - half the fun of plants is experimenting - but I would keep it well watered, shaded, and see if you get new growth at the top. If the branches are completely bare, you can break off the tips to see if they are dead or not - crispy and brown=dead, soft and green=live. If live, you might get new growth, if dead, those you can cut back.