Wow, there's a lot to discuss there. I wish I could be there to help. It's tough doing it the first time without someone that knows giving a little guidance here and there. +1 on Grumulkin's advice about taking it to a processor. If you haven't processed a deer before, it can be quite a task. We do so many that we have it down to a science and it saves tons of money. Be prepared to spend between $100 - $200 for processing depending on if you get anything like sausage. Just steaks will keep it cheaper, but most game processors have a fee if the animal is brought in skin on and they have to skin and quarter the animal as well. Since it is such short notice, I will tell you that your plan sounds good up to the point where you have to drag the deer out that far. They do have inexpensive little "carts" that you can get if you think you will be moving them that far. I've never purchased one, but I haven't had to drag that far on a regular basis. If the animal is antlered, a rope with a small handle tied to it could be lashed to the antlers and help considerably in the dragging. Take regular breaks and don't try to be macho about it. It will wear you out quick. It is up to you on whether you want to field dress (gut) before you drag or not. It will decrease weight considerably, but dirt and leaves can be introduced into the carcass and hams that way. I usually never gut before dragging any distance. I know your deer up there can be much larger. You might consider fashioning a litter made from a couple of poles if it is that difficult. Drag head first.
As for the gutting, here are some pointers.
Hints: Take more than one knife, and one that will cut well through cartilage. Keep water for rinsing handy. A gallon milk jug will work, or a gallon of drinking water if you want to use it for rinsing and drinking. If you see anything that looks like a fluid filled sack, big or small STAY AWAY with the knife.
1. use vinyl gloves
2. start delicately in the stomach area until you cut through skin, the first layer of fat, and the muscle. Be careful not to get too deep. When you see that you are about to cut through the last bit of muscle, try to pull up on the skin (using the hair if necessary). when you cut through and can see the stomach, with your non-knife hand, make a "V" shape with your index and second finger and insert into the hole. Lift up and put the knife between these two fingers with the blade toward the head and pull up on the hide as you cut up toward the head. This will keep you from cutting into the intestines.
3. Stop and the bottom of the sternum. Finish the cut downward using the same technique and continue cutting after reaching where the hams intersect. You can do this now with the blade down while kneeling to the rear of the deer, just slice the skin open to expose the hams. You may opt to leave the skin on if you aren't going to split the pelvis (see below)
4. this next step can be controversial, so I will give you both ways to do this. The traditional way is to cut around the ****, severing the external skin. You can tie the **** with a string and pull this back up into the lower abdomen, cutting the connective tissue through the pelvic opening from the rear, or
5. (I recommend this only if you are gutting near your vehicle to minimize debris getting on the hams). You will need a small hammer and a knife you will use only for this (do not use your good knife for this). I have an old knife with a rounded point that works great (also works for splitting sternum). Cut the meat between the hams, you can follow where the muscle joins and see the white connective tissue between them all the way down to the pelvis. At the top of the pelvis, if you place your knife tip and feel along the edge, right in the middle you will find a soft crease where the bones meet. When you feel a slight give, tap lightly on the back of the knife with the hammer, it will split the pelvis all the way open. You may have to feel around and don't go whacking just to get through. You will know when you've hit the sweet spot. Now you can cut the rectum out easily. Do not pull it up, you can roll it out with all of the guts at the end when done this way.
6. After you have done either of the two above to free the bottom, you need to focus on the chest cavity. If you have a deer you intend to mount do not split the sternum, you will have to reach up into the chest. If it is a doe, you can use your knife (or I choose to have a second knife for rough work so as not to dull the one I'm using to cut) to pull up and split the sternum as far as you feel comfortable.
7. Cut away the diaphragm (the muscle separating the intestines from the upper chest cavity. Tilting the deer to one side will actually help pull down so you can make the cut further back toward the spine. Roll the deer on the other side and repeat with the other side. When you have cut as much of the muscle as you can, reach with your left hand and grab as high up as you can above the heart and lungs where the esophagus leaves the chest toward the head leaving a little room between your hand and the rib cage at the top. Grip this and cut the esophagus above your hand. Keep a tight grip. This will be pretty strong and you can use it to pull all of the guts out.
8. Pull back now and the guts will begin to peel away from the spine, back, and tenderloin area. Use your knife to free any more diaphragm or connective tissue, but be careful not to cut the tenderloins. They will be about 3/4 down and situated on either side of the spine (there are a smaller set up between the shoulders but they aren't much unless the animal is huge)
9. Keep pulling and cutting connections and the guts will pull all of the way out since you have already separated the bottom portion. If you have a good grip, you can usually pick up all of the guts using the connection of the esophagus, heart, and lungs that you have grabbed. Just be mindful if you feel it start to tear to go easy, you don't want it all over you.
10. Dump the excess blood and rinse as soon as possible.
