You sure energy it's the only condition? I think you can only "Do Maintenance" when the maintenance level is >100.
Indeed my healthy routine would be: Save energy in the evening to interact with bartenders/guests; "Do Maintenance" at night, sleep, but sometimes I can't "Do Maintenance" at night so I have to waste a turn: interact sleep sleep.
Unrelated: I managed to persuade a commisioner to pass a law by promising I would hire "her kid" - I didn't have a job opening at the time and the commissioner got mad, so I saved-scummed and open a bartener position before the commissioner came, but then again the only option I had was "I don't have openings at the moment..." I also met "the kid" and consider her for a job but she said she was not interested. So I guess you must have an open position to the kid's liking?