Where To Begin?

There are just so many problems with Orthodoxy that one often doesn't know where to start.

So if you, for some reason, had one chance to convince a believer to stop believing (why? beats me) what argument would you choose?

I guess I'm kind of wondering what the rational order of disbelief is. I mean if one had to completely deconstruct Orthodoxy "from scratch" where would one start? There are so many tantalizing issues.

Does one start from the top and talk about God, and the problem of evil?

Does one quote the rather cruel commandments that hopefully no benevolent God authored?

Does one cite the fact that God either lied through science or in the creation account?

Does one discuss critical Bible scholarship, the Ancient Near East, and archaeology?

Does one talk about the fact that humans wrote (or in this case spoke) the Torah She B'Al Peh?

Or does one just simply say "PROVE IT!"

Which skeptical discussions take logical precedence as the initial "underminers" of Orthodoxy and which ones only become meaningful after Orthodoxy has been rather thoroughly undermined? Some commenters said that my discussion about contradictions in the Torah (hmmm I need to finish that sometime) was not itself an underminer of Orthodoxy (because of TSBP apologetics etc.) but was rather something which one discusses only after having decided for other reasons that the Torah and Orthodoxy in general are not divine.

I dunno

What do y'all think?

If you had to explain it all to someone what would you start with and how would you proceed?