2. Bar job is an early game job, it unlocks after beating first boss of the game. How do you expect people to know "what they're doing" at this early in the game? You can't justify bad gameplay mechanics here because players are simply not experienced yet to know what they are doing. Saying "if you have played this game for hundreds of hours like me you would know how to play" is a very bad excuse for a bad gameplay mechanic.
Figuring it out is half the fun.
5. There are multiple ways of torturing yourself:
Go for a slut run -> Karryn ends up having orgasms just by being stared.
Go for a pure run -> Karryn ends up gaining unwanted passive(s) anyway.
Go for a normal run -> Lose the game anyway because losing the game and playing again with unlocked passives are the intended way to play the game, literally adding another layer of grinding for no reason.
For a slut run: Healing thoughts is mandatory and you can unlock passives which restore your energy when receiving creampies.
For a pure run: You have to complete the game as fast as you can, otherwise you WILL gain unwanted passives.
A good build in NG+ is agi/str unarmed (focus+taunt/cautious or counter stance spam), on a fresh save you can try dex/str halberd (cleave is very good).
Get +order/control edicts as necessary (-8 control is a good mark, not sustainable when you get to lvl 4 though). Skip the +riot chance edicts. Skip the side jobs (except reception, so you can keep up with the -order on later levels). Get stats, halberd/unarmed spec, accessories (the +10 str and the stamina regen bracelets are extremely good for their price) and the problem edicts (thug problem, nerd problem etc.). Rush to the boss as fast as you can.
I don't know what you mean by "normal" run, so you'll have to elaborate on that.
And there are still some unexplained factors to things that are explained there. For example one of the npc's explain that endurance is supposed to decrease sex damage but why does Karryn still take 50% pleasure damage when making endurance build? Is it because of negative sex resist gained from passives? But if that's true than how am I supposed to make a slut build and win the game? Decreased sex damage doesn't matter when Karryn is constantly orgasming at the sight of a penis. Oh that and also you are literally punished for making a slut run because of the amount of negative passives you get. The game is like "Oh you want to enjoy scenes and progress through the game? Too bad, take this passive which makes Karryn come even faster".
Endurance does decrease pleasure damage, but your sensitivity and resistance matters a lot too. The Mind tree has really useful edicts like "Resist orgasm" (self explanatory), "See no evil" (+sight resist), "Hear no evil" (+talk resist) etc. You can also buy accessories and specialization edicts (unlocked from Research on lvl2) which increase resistance/lower sensitivity.
And there are subsidies, which is supposed to be a risk&reward mechanic, turns out it is an instant game over, you literally lose everything if a riot happened when you were trying to earn money from subsidies. The game is like "Oh you are trying to make money in your 6 hours playthrough? Too bad, let me create a riot at the worst moment possible so you lose 6 hours of your life"
On a slut run you only depend on subsidies before lvl 3, after that you go for +income/-expense edicts and sidejobs.
On a pure run your -control will most likely be dangerously high, so your main problem is keeping order up, rather than money. You can do that by clearing rooms and doing reception. Level up as necessary and defeat the boss.