When you linked your save, I just overrode my save, didn't think you'd be interested in the corrupted version, sorry. I can say I was at around 90+ before I spoke to anyone besides the duchess of lyx, I just focused on developing my land as much as possible, ensuring maximum income so I could just auto-generate money and items while I focused on questing. To clarify, I had maxed almost everything at that point (final storage upgrades took longer), I would continue to make planks and tools until around 110 because it was so time consuming, even with the improved ratio, but I started to quest around 90. I had done everything that was possible without going to the elf kingdom (the pirate quest, the barbarian queen, killing the duke, visiting the shrine, getting the nymph blessing, etc). I ended up saving at 160ish and trying to restart to get the orc skull event to fire for lyx, and that's when I couldn't load it. Oddly enough, I had been able to load at around day 140, because I remember screwing up the training with the guard.
In response to specifically the female bandit, I did defeat her, took her prisoner, and noticed I could have her work at the farm, so I did. I did this at the 90+ mark (though I didn't assign her to farm work until around 120), my land was doing well so the 1.2k for a good sword was a cheap investment. While speaking to her, she suggested I remove her collar and brand her, but I couldn't trigger that option (assuming it was an actual choice). If it helps, I also took the other bandit as a prisoner as well, but I could never assign him to anything, my only option was to sell him for money, but I had more than enough so I kept him around, assuming I would be able to assign him somewhere eventually.
As for the cortesan quest, I've visited them many times, paid for services, even gotten the indian girl to dance for me, but my only options have been to be serviced for 100 gold from the start. I noticed in the screenshots, the amount varied from 50 to 150, but mine were only ever 100 gold. I've also tried every option with every girl, hoping that would advance things, but all I could do was keep going.
I'm not sure if this is relevant, but once the church got going I had tons of faith, so I went to the library and opened every book, but all of them after the first one were blank.