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If you're having trouble I recommend staying away from legal money as much as you can. That means avoiding research. Don't build anything that costs legal money. It's really annoying but it's achievable. Prepare yourself by researching things you might need before the quest (like increased radius on warehouses/residences). Place a couple of residences down where you need them because you'll need them to do the work that hotels would otherwise do.
Be very careful to only build with dirty money. I think you can still get away with keeping your upkeep on legal money.
Another thing you could do is build a few things with dirty money to help keep the dirty money ratio high. Build an aerodrome with dirty money or something. You can always get rid of it later.
This is so frustrating, I've spent so many hours replaying the game trying to play right. I have no idea what I could be missing, I tried so hard to avoid using legal money.