Maybe I can help a little. It just galls me that I can't help a lot, since I'm supposed to have a handle on prominent MO guerrillas, and yours passed under my radar.
I examined the six Isaac Bledsoe entries in the online MO State Archives website at http://www.sos.mo.gov/archives/soldiers and I eliminated the last two entries as belonging to an Isaac Bledsoe from Lafayette County who was killed at the Battle of Lone Jack on 16 Aug 1862. I believe but cannot prove that the other four entries are your guy. I say that because that man served in the 1861 southern Missouri State Guard under a Captain Thorp. The best source for MSG officers is Peterson, McGhee, Lindberg, and Daleen's 1995 "Price's Lieutenants." This reference says that the only Captain Thorps that served during 1861 were in the 8th Division, which included Barry but not Stone County. I think it's entirely possible that your Stone County Isaac Bledsoe crossed this imaginary line to serve, however. As you probably saw, this Isaac Bledsoe in Captain Thorp's company served for three actual months and 22 days between June and December 1861, but this cryptic record gives us no idea what he experienced during that time. This is pretty thin, I admit, but I will give it anyway, if it will help.
Now for the embarrassing part (to me, anyway). Other than the brief mention of Isaac Bledsoe in "Borderland Rebellion" (which is taken from the "Loyalty on the Frontier" source), I have nothing on Isaac Newton Bledsoe as a guerrilla or guerrilla leader of Barry and Stone Counties, MO. If someone else does, I wish they would please enter this discussion.
During 1862 the Stone County area was the killing ground of guerrilla chief Alf Bolen, and it is possible that Bledsoe was in his band before Alf was killed early in 1863. I have never seen a list of Alf Bolen's men, however.
I wonder if Bledsoe served as a guerrilla for only a short period--long enough for regional historian Elmo Ingenthron to note him in his "Borderland Rebellion," but not long enough for any other record to survive.
Guerrillas operated in Barry County throughout the war, and I have seen very few of their names in records. Perhaps Bledsoe was one of them.
I just wish I could offer more than this.