The Indian just looks more modern, better finished, the Harley looks like a 1958 model. Ride them both, then decide.
I agree. Every review I've read/watched, the Indian is an overall better bike....suspension, handling, performance (if that's even a category in cruisers), and little things like self locking suit cases. The RK is crazy expensive now....I've seen some leftover '22 SFDH (springfield dark horse) in the $20-21k range. A used 2-3 yr old RK is pulling more than that. New RK is $26k-ish...
You are correct about the chieftain. The chief is a different model in-between the scout and chieftain/ springfield. Its similar to a soft tail for size and layout reference.
Cruisers are 1% specs, 69% what you like the look of, and 30% what you think your friends will like. No shame, facts
Well, you're not dead yet, so I'd say a re-do is on the table. Not that I'm advocating buying a Guzzi...or a cruiser...