This kind of "how to prevent jetlag" question is completely subjective, and I think the only way OP is really going to be able to get an answer that works for him/her is to "just do it" and see. Some people, with the right flight timings, can do pretty well managing the jet lag. Others can't.

For whatever reason, I personally have never found a flight timing to North America that was better or worse for my body at dealing with jetlag than any other. Unfortunately, I struggle every time. So I just book based on schedule convenience. In OP's case, that might boil down to preference for plowing straight ahead versus having an overnight break at the gateway.