This is all very helpful!Well the idea is, that the Kingdom will give you more money to help you "fix" the Prison because the Order is so low. If it is high it seems you have everything under Control so you recieve less help. In short it is a risk reward System since battles are harder the lower the Order but you will get a lot more money that way.
Each Floor has a Soft Timer, that is shown in the Report after Sleeping. Once this moment is reached, you will start to get a Penalty that lowers your Control each day more and more. You can still stay on this floor as long as you want but sooner or later it will force you to deal with the Boss and move on.
Buying Acc. Items is fine. I personally always start with buying 2 cheap Acc. Items on the first day that give +10 Stat Boosts. It makes fights much easier that way at the start. After that upgrading the Bed is also a must have for better Sleep buffs, same goes for Healing Thoughts to restore Energy in Battle. Aside from that yeah you can focus for the most part on stuff that gives you money. Once Order is really low, Repair kitchen and continue to Farm a bit. With a Fighter Build, once you go to the 2nd Floor you should have Slam, Cleave and Skewer.
Well. I just had a bit of a go at it, and did much better. I postponed fighting the boss of the first level up until Karryn literally couldn't level up any more before progressing to the second floor. I am back to having an income of around 300~ unfortunately, but this time I had enough cash beforehand to buy almost the entire first level of training edicts. I don't have any of the skills, but I do have the bar unlocked, and I have the knowledge to know that keeping order high is a detriment, so I haven't bought any of the +order edicts.
I had thought that the soft timer was a 'game over' timer. Glad to know that it isn't anything to worry about.