This is from reddit. A CS rep asked the devs about how passive income works and actually got back to someone about it. So this is how it works in case anyone is curious. It actually clears up a lot of information for me. I wish this information was available in game.
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I’ve done what that dev mentioned, and have never earned passive income or seen the passive income popup 
this explanation was written by a potato and not how it actually behaves. who’s midnight is it using and based on what? if my pc goes to japan will it be a different time or will it use japanese time?
as it stands now. i just the passive income notices every time i go to hq…even going back from a submenu but no income.
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Interesting, I have never seen this screen, ever. I currently have my crew on a plane and am doing missions and when I go to HQ nothing. So it must just be you who gets it every time. Also, I assume they mean midnight UTC, moves devs speak time in UTC.
I normally see the passive income screen once i run the game for the first time next day.
When I had two planes in one company the other plane never made any money, not while I flew in freelancer or employee mode.
After I sold it, bought a second company it started to work.
Now for the second day in a row it made it’s passive income.
Maybe it doesn’t work when you got more than one plane in a company?
However we would really appreciate if Asobo explained this feature in detail.
Hi
Not sure to understand how it works?
Must have 2+ aircraft, 2 companies?
Thank for your help.
I don’t think that you must have two companies.
All I can say is that when I had two aircraft in one company, the second one didn’t make passive income. For the last three days I received passive income with 2 companies (sightseeing & cargo) and one plane in each of them.
I have also replicated this issue, but like you I don’t know if that’s the underlying bug for me with passive income or not. It could be, or it could be something else. Very frustrating issue because we have no optics on what the game is doing with this system
I cant figure it out. Im doing everything the Dev note says. I have 3 companies, each with mulitple crewed planes. Ive been doing hours of employee missions and freelance with spare planes. Everyday I login, No passive income, no insurance payments.
What am I doing wrong? Im about to just reset my career and hope it works afterwards
I got an charged like 64,000 in insurance bills in one day and it wiped out my my currently saved credits, which meant I could not even move a plane to take a freelance mission.
So you’re welcome, I think I paid my insurance bill, your insurance bill and several other peoples that day.
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They made it unnecessarily complicated to begin with…
Just making the aircraft on ‘crew’ generates extra income with flight hours, and adding it to the mission awards each time the player completes a mission would be a much clearer and simpler system.
I just got my first passive income after 100 hours of playtime and trying desperately to get it to work. How you might ask? Well let me tell you. I turned crew off for all my planes. Yup.
This system, is so broken, and so obfuscated. I really am starting to think career mode was outsourced.
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Dude, your my savior lol. After ripping my hair out why im not getting passive income for the past week, I tried what you did. Turned crew off on everything. Next day, get my first passive pay of 900k 
Thanks for the tip, I’ll try it!
Their game is already bugged to death, they are INCAPABLE of giving solutions or correct answers. And the community managers, apart from reframing the DISSATISFIED CUSTOMERS, they do nothing else while the CUSTOMERS are wronged!
Believe me, I’m not going to stop there!
I don’t really like the concept of needing to fly missions yourself to generate passive income. It removes part of the enjoyment from owning a company. I want to own several companies with several planes, leave career mode to go fly for my virtual airline for a couple days, come back and be able to spend the money they earned while I was away. Career mode in its current state just acts as a multiplier for the missions you fly, with a very high cost of entry. Its not really passive income.