I got my first flying job instructing at 28, then went to Part 135, and am now upgrading at a regional almost exactly three years after that first job. Granted, I'm probably going to quit flying, but it was still a fast progression. I also have no debt and no family. Would never have done this if I did.

You CAN, however, make ok money from the start if you stay 91/135. With a family, that's probably what I'd do.