Harold Hill was not as bad as some people say

This has been a fascinating and well-thought-out exchange regarding Harold's character and backstory, and I've enjoyed reading it.

My own take is that he's a lovable rogue who never let his conscience bother him until meeting his match in Marian, Winthrop, and the townspeople of River City.

In Marian, he's found someone who is more than just a pretty face who will melt at his advances. Remember, she resists him at first, and knows from the start he's a con artist, which makes her more of a challenge. The more she resists, the harder he tries, and, as he says at the end, for the first time in his life, he got his foot caught in the door. While he was pursuing his con game, love came in the window.

With Winthrop, perhaps he sees a bit of himself, but I don't think there's anything inherent in the script to prove it. I think he initially sees him as a way to get to Marian (and get more money out of the Paroos), but he eventually comes to like the boy, and somehow just knows instinctively how to draw him out of his shell. Winthrop needs a male role model in his life since the death of his father, and with the attention Harold pays him (even if it's a ploy), he begins to blossom.

Again, he's not a soulless creep or a money-grubbing cheater. He does deliver the instruments and the uniforms, he just has no intention of sticking around and teaching the boys anything. It's strongly hinted that he's morally deficient, and yet all of it's played so light-heartedly (and by such a charmer as Robert Preston!) that you don't really think about the broken hearts and possibly ruined lives he's left in his wake.

The redemptive power he brings to everyone in River City; transforming a town full of petty, gossiping, quarreling, narrow-minded individuals into a united, fun-loving, accepting community mitigates the con. It's not just Harold Hill who is redeemed; it's everyone. Truly a heart-warming and delightful show.