I've had an Indian Roadmaster since 2016. Like most manufacturers, it seems electronics cause most of the complaints, based on forum posts. The powerplant and tranny will be bullet proof. Positives: Easy to change oil and service yourself, smooth ride, good handling and suspension, good power (especially with the 116), adjustable windshield, Ride Command spins up fast, and the bike has a low center of gravity - which makes it seem lighter. Negatives: Adjusting the drive belt can be tedious, seat gives me hot spots, and engine heat can be a bear unless cat removed and/or fuel map changed (however, on the newer models that's been addressed, just not sure how well). I got an Airhawk cushion and that fixed my seat problem.
Nice looking bike - enjoy.