Thoughts on a 390 cu in. stroker from a 318?

If the 365 has enough then that would be the most cost effective. If cost per gain is the metric then the 390 makes least sense. If the 365 isn't enough where are you going to get more torque/ HP in the rpm range that the op is looking at for less cost per TQ/ HP than what the stroker 360 will provide?
Agree, the choice to me is 365 VS 408, if money isn't really a concern then 408 is probably the best move. But if wants to save a few bucks, OP might just have to down shift a little more often and live with the 360. 390 don't make much sense to me for the
OP's stated goals.