You will have a very hard time getting advice on your original question.Most people on this site would rather attack your ideas then offer anything positive.They believe they know it all and what makes sence to them is the only logical answer.
I dont know that your plan makes a lot of sence to most,but it does to me.I like adventure,road trips,and a challenge. I see no problem buying a ride cheap,transfering insurence and plates,and selling it steep after you are done with it.Most people dont know that it is possible to buy a car right,drive it and resell for a profit.
Let them sit behind their keyboards and be negative while you go for a cruise to georgia.If it doesnt save you any money,o well. You got of your ass and did something instead of just attacking someone else.
If I can pull two sitdown pwc through the red top mountains in Georgia with my geo tracker you should be fine with a 4cyl. S10. You only need to do it once,not every day.