In a Hero Book run, you should not do Jobs. I am sure it is doable on Normal but I played on Prisoner Mode, so there I was already pressed without doing Side Jobs with Slut Level. You will get Passives there sooner or later that will make it only harder with doing Jobs but feel free to try. When it comes to money, stay on the first floor as long as you can. There are no Riots, so you can farm a lot of money at low Order. Obviously you need to finish the Floor before you get 20 Slut Level but that should be manageable. Also try do avoid using things, that will get you Passives. Taunt or Flaunt are easy examples. Also never Orgasm in front of someone, since some Passives are blocked as long as you don't. Same with losing a battle, even though I don't think that you have that problem. On the 2nd Floor, even without Jobs you should be in a position, to make 1k-2k Gold a day, if you have farmed a bit of money and then bought a bunch of Edicts, that increase income.
Ye, delaying floor 1 was pretty much the only time i could stockpile a decent amount.
I dont think i can go without taunting, because of the massive bonuses once cockiness becomes a thing, and it also synergizes well with cautious stance, which i use every other turn. Besides, the few passives you get from it help it work better, apart from the idiotic one where you disarm yourself for some reason...
Flaunt i used very rarely, but it helped in moments were i was pressed and needed to stall for a recover. Using see/hear no evil beforehand helps with the enemy jerking off passives a great deal so flaunt seemed ok if used sparingly. Also, third boss and werewolves hit way too hard and at that point even evading drains more stamina than it should, so havin those wanking instead of attacking felt safer.
I think the point where i was invaded and forced to orgasm in front of the guards hurt most than anything else, but if im not gonna be antagonizing them, should be easier to manage. And yes the battles were the easiest part. Would've been better if the game logic didn't translate the act of defending myself against a legion of rape-happy convicts into me somehow being a whore (??).
About your prisoner run for the hero books; were you using a fresh game or NG+? The latter seems like cheating so i wont be doing it unless i want to sandbox in the easy mode.
EDIT: Though in hindsight the game feels slanted towards doing just that - have you fail repeatedly and constantly restart with the extra titles' help, as it does next to nothing to teach you its fundamentals, and the "tutorial" NPC's bait, mislead and in 2 instances outright
lie to you.
Hope im reading it wrong, as purposefully setting up your players to fail, so they'd restart constantly and re-grind everything would be too malicious a design choice, not to mention insultingly disrespectful to people's time.