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actually 2, he has a date you get if you do a large of amount of work to get it.
gonna name the events now how to do them thats something else 

1. Bareshade Expansion in its entirety

2. the farmstead road

3. the werewolf plotline as far as you can go

4. clash with barrel in the bar

and thats it might not sound like it but that is a lot more when you actually are doing it

The problem is that the barrel crash is a random event, which exasperates me because I can't get enough information on how to unleash a possibility of the same happening.

it only happens once, and it happens after you beat the werewolf event as far as you can

(+2)

You just need to finish the werewolf event( having chosen to go after Logan ) and go to the Inn at night, try going in and out since that doesn't advance the clock and you can do it until the event happens