There are tons of trails in the area. The whaleback is in coal township, not ashland. Theres a lot of mud and a lot of tight trails and hillclimbs. Some rocks but you have to look for them.
You do need a permit to legally access the land, but there are also several poker runs every year on this land that you don't need a permit for. They are held by local fire companies and the proceeds go to them. The last one I went on there were over 80 entrants. I would assume that the fire companies would have to get permission to do these, so I would think they would be legal. they are also a good way to learn some of the trails. I would suggest maybe going on one of these or some local clubs have trail rides in the area to see if you think it would be worth it to get a permit.
About the only thing I don't like about wheeling in these lands, is all the trash people like to throw around. There are some local groups that go out and clean it up the best they can, but then they have to pay to dispose of everyone elses trash. And they can't do it.
FWIW, the permit is cheap, considering what you get in return. And is worth every penny.