"If this 1811 male is my Sterling Lester would he be son of James, who was a brother to William the Indian Spy and Dennis of the Donalson Party?"
No, that's not the same James. Unfortunately, there are lots of James Condrys in the records, usually several at the same time and same place. The James posited by some as a brother of William and Dennis is usually the one who married Esther Hibbert (I think). I do not have any proof that they were brothers, though I certainly do not say it is either impossible or unlikely.
The James in the records I posted is down in AL/MS while the other James is found in E. TN, so they are clearly different. Grace McGinnis is the expert on the MS James, and much of what I have on him results from her leads. We know he must be closely related to the family of William the Indian Spy, because both James and William produced children named William H. who lived near one another and named their children similarly. James is a generation younger than William the Indian Spy, but we know the names of William's children from the estate records, and James is not among them.
Given the closeness of the relationships, Grace (and I agree) has suggested that James is likely to be the son of Dennis, brother of William. I suppose he could be the son of one of the elder Jameses, but those people have been pretty well researched, and no one has attached Mississippi James to the TN James. The children we know to belong to Dennis are Pherney and Hamon, from the deed signed by Dennis and wife Elizabeth. And we are pretty sure that Sandel is the daughter of Dennis, since he signed her marriage bond. I also count Isaac among Dennis's children because of their continued proximity in the Grainger Co censuses. There is also a Grainger Co. Nancy, who is likely the daughter of Dennis.
And there is a William Condry who married Nancy Stanley or Stonly November 15,1804 in Grainger Co and died apparently before 1830; Nancy, a widow, then married Josiah Smith. He may also be a son of Dennis.
But even if we attribute all those to Dennis, there is still plenty of room for James to fit into the list.
Perhaps with continued work, we will turn up a record that proves or disproves the hypothesis.