If someone would ask that question from me irl, id answer with JUST FUCKING TELL ME ALREADY!!!
Hah, yes, this.
(Just dispense with the choice altogether and hit me right between the eyes with it. That's what I prefer because then I don't have time to anticipate and get wound up and nervous - all the fight or flight energy goes towards the actual problem).
Classify them in terms of urgency and resource requirements and I'll be the judge of the qualitative aspects.
Otherwise you might as well start by the bad, except if the good is needed to fully understand the bad ( 'we got X but Y which is a segment of X didn't work out as we wanted'). The otherway around applies as well, don't start with the bad just for the sake of starting with the bad if it's a subset of the 'good news'.
Then again that's all common sense and people do it more or less reliably without having to go through any kind of formal logic on a daily basis.
Expression of the post modern paradox : "For the love of god, religions are so full of shit"
Theory is always superseded by Fact...
... In theory.
“I’d hate to die twice. It’s so boring.” Richard Feynman's last recorded words
"Great is the human who has not lost his childlike heart." Mencius (Meng-Tse), 4th century BCE
Good and bad are relative. I'd rather hear the facts first and then decide.
Besides explicitly saying "good news" makes me develop very high expectations (and then I'm disappointed) and saying "bad news" makes me extremely anxious and panicky (and sometimes my very morbid imagination is disappointed afterwards as well ).
My overall preference is to just be told the news and I will decide if it's bad or good. I get irritated when people do this to me. 95% of the time it's because the person just wants an excuse to be melodramatic and they get off on being the bringer of bad news. Pass.
Also good and bad are subjective and relative to each person.
Example, one of my employees came up to me last week looking like someone had not only run over their pet dog but had sex with the corpse as well. "Saturned, I have some bad news." Me (feeling mildly alarmed), "Uh, ok, what's up?" Them, "I have a doctor's appointment next Wednesday and so I may be late by 30 minutes... I hope that's ok!!"