Hmm, I disagree about recommending TJ's route first. You appreciate and enjoy that route more by knowing the cast's friendship and dynamics, and about that event. I remember the contrast to other routes to be particularly satisfying in TJ's. I really think you ought to finish at least 2 of the other routes to experience this contrast in full glory.
In general, you tend to find the routes you play later to be richer, mostly because of the ommitted context and details you discover other routes. With that said, I recommend one's first two routes to be Carl's and Leo's. The build-up for their pay-offs are relatively self-contained in their own stories, compared to the others which have their build-ups more connected to history and the interweb of relationships. That is to say, the other routes benefit more from being played later.
I'd personally recommend: Carl, Leo, Jenna, TJ, Flynn
P.S. When they said 'check out the Smoke Room', they meant a separate game (unless they wanted to see the world burn).
EDIT: I've resolved the order after some consideration.