Hey Steve. How are ya?
Yes, somewhere along the way I recall reading on the net that Lightfoot did express some interest in jazz but I didn't know he had actually experimented. When I first heard the dissonant bass chords of Oh Linda punctuate the air I was immediately taken back to one of the jazz clubs in Chicago I used to enjoy. Groovy, man, groovy

Admittedly it took me off guard. But I found it to be a wonderful surprise and loved it almost immediately being a lover of jazz and blues to begin with. And his "dabbling" within this genre is pretty impressive. So a definite *yes* to your question, it would have been very interesting if he had produced a few more songs like this. He captured that jazz mystique quite well!
Unfortunately DSR is not yet a part of my collection but now I'm curious to hear this similarity you mention. Yes, I am much like the kid in a candy store, not sure which way to turn next!
Another one that has quickly become a favorite is Sixteen Miles (To Seven Lakes)
Jennifer