I already have a drain on my pan, though I'm going to put a deeper pan on when I change the filter. Stock pan is twisted too much and doesn't seal very well.
From what I saw on the "better" filter, it is just the "cheap" filter media with the plastic encased around it. Not sure if that is the case. The "better" filter was $13, cheap one was $8. I have a resuable Mopar gasket, so I just checked the prices on the filter, not the kit with gaskets.
I change mine every 15,000miles (same as the diffs and T Case) which ends up being about once a year.