Have a 2014 Overland. Great vehicle. 84K miles. Only routine maintenance. Have the V6. It's not a rocket, but passes well enough on 2-lane roads. Interior leather shows some wear, but not as much as many other cars I have seen with similar age/miles. Enjoy your ride.
I had a Crossfire convertible. It was a great car. Be sure to check the window in the convertible top - the adhesive is a know issue, particularly in hot weather.
You can find loads of information on an excellent forum dedicated to the crossfire:
https://www.crossfireforum.org/forum/
You will like the canister filter. Less messy and you can examine the old filter without cutting it open. I would buy the Mopar filter.
DIY: https://www.youtube.com/watch?v=_ezpAEzy2Io
The seller has 2 x 55 gallon drums of oil. That's 440 quarts. If the buyer pays $500, that works out to $1.14 per quart. I'm not interested in it, but the buyer is not being hosed for purchasing some history.
You'll need to reset the clock / radio station memory. Nothing else that you will notice. The transmission does adapt to the driver, but you will not loose any important learning it has done.
You want HOAT (like G-05).
Your user manual can be downloaded from here:
http://www.dodge.com/en/owners/manuals/
From your manual:
Please review these recommendations for using Hybrid Organic Additive Technology (HOAT) engine coolant (antifreeze). When adding engine coolant (antifreeze):
•...
Scroll the down arrow on the left side of the steering wheel (EVIC controls) until you read Vehicle Settings. Press OK and scroll to Security. Press OK select Speed Warnings. Select desired speed or Off. Press OK to return to original EVIC display.
I really like the cartridge filters that are becoming more common. They are easy and less messy to change, and allow inspection of the old filter without any cutting. Below are a L36135 with over 7,000 mi and a L36296 with over 8,000 mi.