Gavra,
1) Yes, I wasn’t trying to argue with you (for a change).
2) I know you’re passionate about differentiating between ikar had in and chumra, but I don’t think there’s a huge one in the context of our discussion. Halachos which are meikar had in can be used manipulatively, and chumras can be taught and implemented lovingly.
For example, if a parents wants their child to do the right thing because of
how his behavior reflects on them, the child will sense it and could rebel. If a father practices and teaches chumras out of genuine yiras shomayim, the child is likely to keep them b’simcha.
Regarding the OP as well, an at risk kid doesn’t necessarily feel any more stifled by chumras than by halachos mi’din.
3) I know you agreed, but I think you mentioned that the OP was only talking about chumras. You wrote “The issue is how to be flexible within the Torah’s guidelines.”. I understood that (maybe erroneously) to refer to the OP’s issue.