Dear Avira,
No thanks. I have had more theological conversations with more gedolim than probably any kid ever. It’s for the lazy or the simple minded. It’s not something great people enjoy. Whenever my conversations got sticky, I just leaned on Aryeh Kaplan. I have yet to meet a great person who is willing to dispute Kaplan. (Though I know of two great people who openly disagree Kaplan’s opinion. One I will probably never meet. And the other we couldn’t get a discussion going. It was just yes. Why? Because. And if it’s no, than it’s just no.)
Now you seem to have no depth on this issue. The Chovos Halevovos requires serious philosophical study. It means something completely different when it’s superficially referenced. And only the well rounded, super geniuses among the gedolim had any interaction with the haskalah in the last fifty years. Already a hundred years ago, haskalah was barely a factor. You have everything all confused into a big mush. Because you have never seen the weaker elements of the Yeshiva Community. You just write them off as not yeshivsh anymore.
The main point which I think you should agree to, is that a lot of the meshachist stuff is silly. If someone believes that, why bother with them? Let them feel safe in their beliefs so that they would be comfortable to get involved in other topics. Eventually they would wizen up. And if they don’t, then it’s not much of a loss to begin with. But doubling down like you do, just makes them be more defensive. Then they hesitate before learning anything new because maybe it will ruin their belief in the Rebbe. And all their creative intelligence gets wasted in more elaborate defenses.