I don't agree that bet on flop is bad here. OP said that Villain is a good reg. Good regs call BB with a wide range. It is not really too much of a mistake to bet near 100% on flop vs. BB caller due to range advantage. I probably would choose 1/2 here, but 2/3 is okay.

If there is any part of the hand that I'm not a fan of is re-raising the turn. I feel like this is pretty big mistake. When people check/raise OOP on the turn with a rainbow board like this it is usually a really strong hand such as a set or strong 2 pair. I don't like betting the turn either. I think it is better to check back and take a free card to hit a possible str8. Your opponent might make a bluff if a str8 card comes on the river.

I've never understood the mantra of "if you bet this street, then you must bet the next street." If you have hands that bluff the turn, you need to have hands that give up on the river. If you don't, then you may as well just shove the turn. In OP's case, he says he knows that if his opponent is calling the turn that he isn't giving up on the river. This means he shouldn't bluff the river.

If OP had a read that his opponent would fold to his bizarre bluff then making the "bad play" can actually make sense. However, I think it is more likely that OP is suffering from fancy play syndrome since he knows that BB is a good player. Sometimes when you're up against a good player you feel like you need to do something spiffy to outplay them, when really you just want to play your A-game.

Most people with a strong hand in your spot would probably flat all their strong hands to his raise so it may appear a bit sketchy.