Responding to some odds and ends now: I don't have the specific dates of Quantrill's trip to Virginia to seek a high ranking commission. Guerrillas were controversial among many senior officers, and I can well imagine Q. being cold-shouldered. Price, however, was happy to have Q's forces scouting for him. Missouri guerrillas tended to operate in smaller bands, coming together occasionally for bigger operations. George Todd, Bill Anderson, Dave Poole, Archie Clements, Fletch Taylor and others would all have led small parties at times, and reorganized with each other at different times. Clements is most closely associated with Bill Anderson. John McCorckle's memoir talks of riding with Q, with Todd, and with Dave Poole at various times. Before the Lawrence raid, Q called all the bands together for a war council. He used revenge as a very persuasive motive to convince the men to go to Lawrence with him. This suggests to me that he had the respect of a lot of the guerrillas at that point in time. I think Quantrill was actually quite popular with many of his men--at least at first. He was popular with many of the civilians along the western counties of Missouri, too. During the winter after the Lawrence raid, his command began to fragment, with Anderson and Todd both breaking off and each going his own way. Ironically, I don't think Quantrill was savage enough for their taste by this point. In addition, Todd and Anderson were ready to kill each other by that time. Quantrill is usually demonized by writers, but I think Anderson and Todd are responsible for most of the excesses committed by the overall group. Certainly, Q. was not responsible for the blunders at Fayette, the massacre and savage fight at Centralia, the Rawlings Lane fight, or the infamous meeting with Price in Boonville. Quantrill was essentially on extended leave and semi-retirement with Kate King in a cabin up a very long and deep hollow in Howard County, several miles upstream from Boonville. Several of Q's men left the band after Lawrence and went into service with Shelby. It's possible that Lawrence was too excessive for them, and it's equally possible that it would be easier for them to avoid Federals if they were part of a larger group. It's very hard to say for sure.
Regarding the reunion photos, there are several, but this is one of the more interesting ones to me, because John Noland was still alive and in attendance at this reunion. He is the black man at the right end of the back row. He was something of a celebrity along with these other guys, but when questioned about Lawrence, he insisted that he had scouted the town prior to the raid, but that he didn't participate in the raid itself. I am not sure I believe this version that he told to Connelley, but I think he's a fascinating character. In fact, my own search for information about him is what first brought me to civilwartalk.com.
@Booner found some old census records that strongly suggest to us that Noland was a mixed race man, and perhaps the nephew of Asbury Noland in the Independence area. He might have been the half brother of the Noland brothers who joined Q's. group. I can envision them all heading off to fight together after a jayhawker raid. The other guys were celebrities, too, as @archiclements has said in a previous comment. They were often sought out for newspaper interviews and such. Some turned to the outlaw life after the war, but most of them resumed normal life as best they could.
Regarding Harry Truman, his uncle by marriage was Jim Crow Chiles--a well known guerrilla. Harry's grandmother had been raided by jayhawkers so it was natural for members of his family to have harsh feelings about them. One of my favorite stories about Harry was that he would go to Kansas periodically and his mother would say: "Be sure to look for your Grandmother's silver while you're out there."