Start by getting rid of the so called "Crush Proof" gaskets.
It appears to me they are using an RN-8011 material which is fine for sealing irregular surfaces. However, it will tend to wick oil (weep) and not maintain bolt torque (weep some more).
If you want the straight shot on the best way to install the Milodon gasket I suggest you contact the manufacturer for their recommendations.
And as far as I know the jury is still out on just how well that Jeg's tray seals on certain oil pans.
If you want a real quality gasket click the link in my signature and browse the catalog.
