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I haven't had one of these jobs generate outside of a business, such as a Diner.
And in those cases, a few minutes after the call, someone matching the description given would get up and walk out of the building carrying a briefcase, and I'd have to follow them.
The actual exchange would take place in some side street or intersection.
But every time, the person would leave the building they start in, so I'm not sure if the exchange can take place in the same building, but on a different floor.
But, again, I haven't had the job take place in some multi-story place such as the City Hall.
I'm on my sixth playthrough with about 100 hours in this game, and I think these tail & acquisition cases are buggy. I remember picking the Tail & Acquisition case five times, and three out of the five, the person with the briefcase walked out to a street somewhere and stood still forever. I know that someone is supposed to come to meet them, but that person never showed up. The other two times I tried the case, it worked properly. But three out of five times is a high failure rate, so I just don't pick those missions.
I followed the initial carrier, I took a photograph of the exchange (though no people where visible on the photograph o.O) and tailed the recipient to their appartment. I took the briefcase, identified the recipient, set the photograph up in the case file and... were not able to request a route to finish the quest because something would be missing.