Is it feasible to Uber to the venue and back home easily or are there too many cars to make it a hassle?

Uber and Lyft drop-off and pickup is in front of the Convention Center on Salisbury Street. There's a pull off area in front of the Convention Center, which is safer than stopping one lane of the road in front of the Amphitheater.

People Uber at every show. Never seemed to be any hassle to get home

Danielle is correct