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(+2)

Assuming you updated and aren’t in a version where it’s impossible.

You have to take over the Old Club to be able to clear the roadblock.

Old Club doesn’t appear initially in the map, you have to interact with the outskirts icon and talk to Jessica about it.

Old club was one of the first things I did. It didn't show up as a boss fight. I conquered the mansion and then it let me try the old club when I tried to go to the outskirts.