Rick - Wish I could give you a better description of my impression of his music, but I'm one with little musical talent - I just make a great audience! I guess that's why I like to research these things, because that's one way a non-talent person can become involved with the music I love.
But to answer as best I can... He played for about an hour in kind of a club setting, and I was there with an older brother who lived in Chicago at that time. (I think it was 1946, which make me about 14 at the time; that's another reason for poor impressions!). I seem to recall that he was there to record with some of the great blues players of the area, but I'm not sure of that. I do know that after the hour or so we went to an upstairs hall a couple blocks away that I later in life found was a not-so-nice private club. What I really remember to this day is that it seemed like two different people played under one name. During the first show, he was pretty much what I hear on recordings. In the "club" it was more of a jam session, with several people singing along, and a few playing. There he seemed totally different. His voice seemed to change on each song. My Dad was a fine "Irish Tenor" singer, and on some of the slow stuff, Huddie sounded the same way - soft, gentle, high tenor. On some of the "rougher" ones his voice was rough and raspy. And on some sad ones, it was almost a lower register whisper. Part of that might have been that he was not in the best of health, although we didn't know that till some time later. But I guess what I remember most was that his music included ALL of him. Body, voice, and if I'd have been older I'd probably have included his soul were pare of the music. My brother (who would have been 36 at the time and a big fan of his) said he was taking me because I needed to know what a musician sounded like when he sang from the heart - not a bad description.
Hope you can make some sense of this!