Seriously at my wits end

Is it the factory pan? I used to have an old dodge ram that had a constant issue with that as well. My factory pan was bent in some areas and would not seal with the reusable gaskets. So I ended up just getting a generic gasket and gooped ultra black on it, then I installed the pan slightly tight and let it set for a few hours.
I tightened the pan bolts to specs afterwards.
Had very little problems after that.