I think that Chrysler is going to have a really hard time becoming a high-volume brand again (I would love to be proven wrong, but I just do not see it). They have been out of too many segments for too long, there is no obvious role for Chrysler in most segments (unlike Dodge, Jeep, and Ram), and I think most of their buyers have moved on to other brands.
If they are going to be low-volume and an EV brand, they might as well become a high-margin brand directly competing with vehicles like Tesla and Cadillac's EVs.
Rather than a re-skinned Charger sold as the Chrysler 300, they might be better off producing a new Chrysler Concorde as a Model S competitor, especially if, as has been reported, the styling of future Chrysler vehicles is going to be based on the Halcyon concept.
Instead of the "brute in a suit" upscale muscle car that the 300 has been and would be, the Concorde could focus on minimalist styling, aerodynamics, luxury, minimal NVH, comfort, and cutting-edge technology (like the Concorde jet). And it could still be fast, but more like a Model S Plaid than like a Hellcat.
Leaning into the Concorde being an EV could actually simplify its design. The Concorde could still be based on the Charger Daytona (including the 800-volt drivetrain, eventually) but being an EV only would eliminate the need to accommodate the Hurricane I6. Giving it a low hood and pointy nose like the Halcyon concept would eliminate the need for the R-wing, and reducing NVH would eliminate the need for the Fratzonic chambered exhaust.
This formula could be replicated in other segments, with much of the engineering for Chrysler's low-volume, high-margin vehicles being already done for their higher-volume platform-mates. A Chrysler Airflow D-CUV (Model Y competitor) could be based on the Wagoneer S. A full-size Chrysler Aspen CUV could be based on the upcoming STLA Large Durango/Stealth. A Chrysler Portal C-MPV could be based on the upcoming STLA Medium Compass. The upcoming Pacifica EV could share its body with a new Chrysler Voyager (which would be the exception for the brand's formula, being priced lower and with HEV, PHEV, and/or ICE drivetrains to attempt to retain the brand's current, traditional minivan buyers). All would be EVs (except Voyager) with Halcyon-inspired styling, aerodynamic designs, minimal NVH, and the latest in safety, autonomous driving, AI, and connectivity technology.
In order for this strategy to work, execution would need to be flawless. Styling would need to be jaw-droppingly beautiful, technology would need to be mind-blowing, and quality and reliability would need to be beyond reproach-- a daunting task indeed. Introducing each vehicle after its higher-volume platform-mate would allow Chrysler to have most engineering and production kinks worked out.
Chrysler as a Tesla fighter could potentially find buyers outside of the U.S. and Canada in markets like China and the Middle East and, to a lesser extent, Europe and Australia, making Chrysler more of an international (but still low-volume) brand.
These vehicles would obviously not appeal to traditional Mopar enthusiasts, but targeting a new, smaller, more affluent audience might be less risky than trying to re-enter high-volume segments that have left Chrysler behind. The Mopar faithful would still have Dodge, Jeep, and Ram to provide the kinds of vehicle they are passionate about.