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The briefcase is on the roof of the gazebo, and you need to use the broom on it to knock it down.
The key is secured to Patrick's ding-dong. You'll need to do a bit of the Rachael/Patrick route in order to access it. There's a nice guide here where, under the Patrick (Screw Him Over) section you can find a walkthrough on getting the key.
Once you've secured both items, you can unlock Compubrah and inquire about Patrick's business engagements. An achievement guide located here lists the conversation responses if you get stuck.
I don't think it matters whether or not you screw Patrick over, because the achievement itself is about getting access to Compubrah and going through some dialogue with it.