I'm assuming you've been using the AutoWin option for every fight? You need to make sure that you're running the latest version, and then get into another battle (AutoWin or not, doesn't matter - I patched the glitch) and then sleep until you get Lily's event.
As for the roadblock, what are you stuck on? You just have to reach it, search it, conquer the new Old Club location that appears and then return to the roadblock to clear it.
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I don't think training fights will work, as I think I designed them to restore your health after you were done, but maybe..?
A guaranteed way to get it to work would be to switch your meals (via Hana in the kitchen) to "Caviar on Toast" which gives you a 50% chance of your territories being attacked by Org Goons.