I would replace both of them, especially if you've never done it before or if you recently bought it from someone, used. Never know if they even did it. I happen to be doing doing some research of same exact thing. From what I've read, it doesn't matter the brand that you go with for the regular trans filter but for the twist on one, you'll want to go with the mopar brand one. Reason being is the mopar has an anti drain back valve in it. Other brands don't so when your truck sits overnight, all of the fluid drains out. When u first start it And try putting it into gear it won't go for a few seconds because of the drain back. I hope that makes sense. As far as the transmission pan, the key perk in my mind is draining most of it out without having to slowly lower the whole pan down, TRYING you best to not spill it all over the place. If you didn't want to buy the whole pan, they do make drain plugs that you can install in you OEM trans pan. While you're doing that, might as well get a transmission temp gauge and sender and hook it up too. Unless someone has finally cracked Chrysler/dodges enhanced PIDs lol. Good luck tho bud

edit. I did read on another forum that a couple of guys only change the filters every other drain and fill.

 

1. Two filters yes. Suction and return. Ensure when replacing the suction (big flat) filter that you get the metal ringed rubber grommet it sits in out too. Some people will actually try to shove the new grommet into the old one then wonder why their truck won't move...OEM filters are the best for these, while converter drainback doesn't hurt anything it's inconvenient having to wait for the pump to refill the TC before you can move.
2. Yes.
3. F@ck yes there is, makes it helluva lot easier to drain then remove vs undoing bolts and letting it sag to dump the fluid. ALOT less mess.
4. More than likely, however OEM from the factory is actually sealant, like permatex or similar.

Both my Superchips tuner and the Aeroforce Interceptor gauge I have mounted will read the trans temp PID.