Man this game has a pretty good gameplay loop, but it's way too overtuned. Trying to get stuff done without save scumming is an exercise in futility. You need to tone down the bad rolls by a lot and increase work point gains. I don't even know how to get lewdness up for the sucking cock training because she always brings it down at the end of day report.
She shouldn't, unless her Resistance is too high. That might be the case if you tell her to do a lot of stuff day after day after day
OR if you are at a special point in the game where she starts building a super insane amount of Resistance to force a scripted game-over.
Basically, you should do this:
- always keep at least 30-40 points just in case you fuck up and she cancells a lot of them, to not end up with none at weekend.
- do a weekend "Deal with her" thing, it provides an everyday Resistance reduction. Feel free to fuck her up during the week
- if things are getting out of hand - let her cum (unlock her) - this will help a fucking lot. And keep her unlocked until you gather points again
- develop buffs, get help from Carl
- once you have a special level of cum-slut buff, it should be easy
- if the game is too hard - die several times - you'll get a noob-buff to help you with Resistance