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IreneSwift From what I've read, stakeouts have been unreliable for a long time, maybe not since Ambitions was released but certainly going back to 2011. It seems that the case-related stakeouts are not impossible to complete, just unreliable, with the player sometimes needing to repeat them a number of times before they work.
Or you could use NRaas DebugEnabler to assign the next step of the case, bypassing the stakeout entirely.
For the issue with the police station, try MC reseting the lot, when your sim isn't there, of course. I don't know whether this is the same problem as with other rabbithole lots, where the sim and any others on the lot get kicked out, but it's not uncommon.
As for the benefits of playing a PI, I don't think they're supposed to be monetary. The fun, if it's fun at all, is in playing an active profession, not to mention the campiness of the cases and dialog that goes with them. At least the weekly stipend increases though.
I tried resetting the police lot, but it still glitched out and sent him home on the "psychic" case, which he still keeps getting. Other cases that involved helping the police with their caseload or specific cases seem to work just fine. So I simply turn down the one that doesn't.
I'm being more patient with stakeouts, and he recently succeeded with one on the fifth try. I did finally find out how to get him to write a stakeout report, and he gets paid $450 for those, so that helps a lot.
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