Marian and Matthew,
You need to be cautious what you believe about Quantrill during 1861, since about the only source I could figure out was Quantrill himself. Connelley did not share his sources about Quantrill with Captain Mays' outfit in the Indian Territory or Quantrill at Wilson's Creek. The only source Connelley mentioned in that page was Quantrill himself. The only other sources I have seen about Quantrill during this period were from guerrilla memoirs quoting--guess who?--Quantrill. Edwards wrote about this, too (page 51), but you need to remember that Edwards' sources for this information were probably guerrillas, too, since Edwards interviewed them extensively for his "Noted Guerrillas." What I am saying is that there is little solid fact about Quantrill either in the Indian Territories or at Wilson's Creek during 1861.
Now, is it possible that he did indeed do those things in those places that year? Sure! It fits the pattern of his behavior. I would not be surprised if somebody found solid source verifying at least some of this. But for now, this is unconfirmed. Maybe true, maybe not. I want to believe, but I want to believe a lot of things, and that doesn't make them true.
Marian asked about why the Jackson Countians accepted Quantrill as their leader even though he was not from there. I agree with the reminder that his schoolteaching experience helped. Several of the guerrilla memoirs state that Quantrill had natural abilities to lead, was cool in a fight, had charisma and was very convincing, and showed natural abilities to chart the course for southern resistance to Yankee occupation of west central Missouri. Connelley and some other Kansas sources also give us clues that Quantrill's prewar "Charley Hart" days as a roustabout, slave stealer, and etc. show that Quantrill loved adventure and demonstrated daring to the extent that he seemed to get a thrill out of flaunting civil law in eastern Kansas at those times. These wild days also prepared this Ohioan for a later life as a leader of guerrilla fighters.
Also, Quantrill was a storyteller deluxe, and a convincing one at that. His story about being waylaid prewar by Kansas jayhawkers who murdered a brother he never had swayed a lot of feeling with the Jackson Countians. I think he told these whoppers to explain why an Ohioan would care about the southern cause. Further, Quantrill's performance leading these men in fight after fight backed up his words with the proof of action.
I personally believe Quantrill was what we used to call a "soldier of fortune" as well as a very effective guerrilla leader. For Jackson Countians he was the right man at the right time, and this outweighs the "windies" he told about what he did during 1861 and prewar.