Thanks everyone.
So basically the main reason for going on the trip, other than visiting my favorite country of all time again, was to experience the aurora borealis (the northern lights). Of course with my luck, I didn't succeed, but took every opportunity to enjoy the trip over and beyond just trying to see the northern lights. With the thought in mind of seeing the northern lights, I told myself I needed to adventure and try to seclude myself from city lights, etc. Of course Iceland is fairly sparse when you get outside of Reykjavik for the most part, but I did want to travel a bit off the beaten path of The Ring Road (route 1) which is the main road that loops around the country. I ended up going the old fashioned route of surveying my opportunities and track via a traditional paper map. I came up with a plan about a month prior to leaving on my trek, picking out key spots that I had heard of before or saw as interest points on the map. Knowing that I would have a versatile vehicle, but not knowing necessarily what conditions the roads would be until I came upon them, I just had to keep an open mind and an open map. With knowing my own personal points of interested I wanted to see, and also trying to venture off of the beaten path, I would say I used 85% paper map and 15% GPS for the whole trip.
The winter is a tough time if you're wanting to get into the highlands of Iceland, and for the most part impassable. This is where I would recommend a guided service, or at least 2 vehicles plus with a lot of winter off-road experience. Although 'off-roading' is prohibited in Iceland, just trying to traverse a marked road can be extremely challenging. There are classifications of roads in Iceland from single digit roads (The ring road being 1) to 4 digits. Prefixed F roads are pretty much closed during the winter, and requires a 4x4 vehicle due to water crossings and difficult terrain at times. While traversing some of the 3 digit roads, and even the 2 digit roads, I was alone for a great deal of time with no other cars in sight. I didn't check to see if I had cellphone service, which I'm pretty sure I wouldn't have had, but did always carry my SPOT GPS with me for security. Of course being outside of the main road, you always want to watch that fuel gauge, as fuel can be limited in some areas.
Two sites I recommend when traveling during the winter in the search of the northern lights are the following:
Current Icelandic Road Conditions -
http://www.vegagerdin.is/english/road-conditions-and-weather/the-entire-country/island1e.html
Icelandic Aurora Forecast -
http://en.vedur.is/weather/forecasts/aurora/
If anyone has any questions at all, feel free to let me know. I've done quite a bit of research, and do know some good spots to stay in the southern region of Iceland. Biggest thing is to remain within your limits, and just go out and have fun. There's lots to see out there!