You mean you don't date your slaves? Because when you date them you can train/study/rise charm.
Wits have a huge impact on chest lockpicking, you don't need to have a lot, around 40 is enough with thief.
If you don't train your slaves no wonder you struggles so much. A tips: growth is very important as it affect how fast you can level up.
Any slave below average in growth is not worth having, good or higher is perfect, you'll see the difference instantly.
On another note I have done a run with prostitutes, upgrade capacity to have 10 people, no fishing and finished the reputation quest on 3 guilds by day 24 easily (the 4th is the servant and guess what, I go with them at the beginning) (oh and by day 24 I had 3k+ already).
On the first 2 weeks I had 3 prostitutes. MC + Daisy and 2 others slaves going dungeons, didn't even bother fishing when they returned.
3rd week I bought another slave for prostitution and that's all.
Doing the reputation quests on easy/medium.
Workers needing a tool? I bought it in the shop, refresh everyday.
Mages needing a beer or whisky/ aphrodiacs? same. I buy them each time they appear in the shop.
Fighters wants something dead? MC is here with his squad 2 frontlines/ 2 mages/healers and the job is done. My equipments? All bought from shop, no need for something at 1k gold, any cheap weapons are a direct upgrade to your DPS then you use what you got from the dead/dungeons. I tend to favor armor first for survivability, need less healing.
In this run I typically buy daggers, there are surprisingly efficient and very cheap.
I have done those runs multiples times, no cheats needed, no impossible quests to remove.