First of all, Rich, I admire your striving to learn this advanced musical form. I'm curious, did you take this on with a working foundational skill level and knowledge of jazz chords? If you don't mind, what would a first lesson be like? Sounds challenging AND rewarding. I hope you really enjoy whatever you can get out of it.
Dave
Jedzep (I like your ID), I've wanted to branch out from folk style for a long time (not that I don't still love folk style and the flat top guitar). First, I didn't understand the history of the archtop guitar and how important it was/is to the history of modern guitar styles. I was under the impression (delusion) that the archtop guitar was a weaker sounding version of the flat top guitar -- a poor cousin so to speak, and not so sophisticated as the flat top. That impression turned out to be far from the truth. I thought, without a round hole on the top, the power of the guitar's sound wouldn't truly escape from the body. I have learned that the archtop evolved during a specific period during the evolution of modern American music, based on the demands of the listening populace and the performers that played for them. And, that the archtop guitar continues to be played in all the styles it is capable of, which is to say practically everything -- depending on the inclination and skill of the player. Because the archtop's construction, when well made and in the hands of an excellent luthier, is formidable in standing up to all sorts of physical and environmental challenges/abuse, we are fortunate to be in a position to play archtops from the 20s onwards that have retained their playability and structural integrity. The challenge is that if you wish to play a beautifully preserved example of a 30s - 40s archtop, you need to be prepared to somewhere from 4,500 onwards, depending on the make, model and condition. Having said that, one can begin with small steps and pay less for a so-called "lesser known" brand form the same era. All I can say is, when it comes to the subject of vintage archtops, you get what you pay for in sound and tone, if you're careful about condition versus price.
Now, to answer your question about my skills. Yes, I have been playing folk style since about age 12 (off and on, more recently very much on). I also have a background in music study with the piano, clarinet, saxophone and guitar. So, it wasn't too intimidating for me to say "I want to learn jazz and swing style. My teacher, Romain Vuillemin, astute teacher that he is, immediately figured out where I am in terms of my skills, and led me in the right direction right away, last Sunday. Knowing where you are in your development and where you want to go is very important. Then, it comes down to practice, practice, practice, based on the belief that all of us are capable of achieving a goal if you set your mind to it!
I agree one can say that the style of swing/jazz guitar developed from the 20s and 30s onwards is perhaps a form of "advanced" guitar method compared to "cowboy chords" on the flat top. But, but, but, guitar playing styles are ultimately interrelated. What I mean to say is that whatever guitar skills you possess now can be extended and practically applied to almost any melody. Most importantly, one should not second guess one's guitar playing abilities, and realize that most of us are capable of advancing our skills by the good ol' fashion method of practicing the daylights out of the song and the guitar in your lap, while imagining accessing versions of the notes in other positions on the fretboard.
My apologies for this long digression.