His original allure wore off once he learned how to really work, because the roster by then was filled with guys who could work even better. Lynn, peak Taz, peak Sabu, RVD, Storm, etc. The WCW mess and return were the best things that could've happened to him, because he was 1) a familiar face to the faithful after so many talents were leaving for the bigger companies, and 2) able to parlay his "loser" gimmick into the Sinister Minister stuff and then directly into the Unholy Alliance.
He also had a massive hand in the way modern wrestlers work, having been the principal trainer for the SAT, Amazing Red, and a few other of the NYWC indie guys that made waves for their insane spotfests back in the early CZW/ROH days.