Isn't shipping turn something like $48 into a pot of like $24? (Effective, after rake.) I'm not sure we'll really get many crying calls there. I agree that a T can't fold, but he's stacking off regardless. I don't think any flush draws call that massive an overbet. Think Ryan Fee mentioned that loose players look for excuses to call and tight players look for excuses to fold. Maybe you're talking about leveling here, but encouraging a tight player to fold by overbetting seems kind of counterintuitive when we want him to call.

With a T on the turn I'd be fully committed regardless of there being some money behind. The question is if we can rely on the opponent to help us build a pot. I suspect not because he's been characterised as a nit, so checking to him to let him bet wouldn't work on either turn or river. We do have to get crying calls, but double pot sized overbets I'm not sure will see many of them.

In the hypothetical case where we are guaranteed 100% to stack off, a flush is good and he has 9 outs he'd be correct to call up to $17 for implied odds. If we bet $14 or $12 maybe he'll man up and shove his flush draws on us in the hope that he has some fold equity and outs if we call.