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I'm stuck at 10 influence and can't get the two proposals at 11. Is that as far as I can go now? I'm still not at the end of some questlines (e.g. Rachel) but I seem to need those two 11 influence proposals to complete it. Any hints?

(+1)

Make a deal with the old man, you don't have to screw over the student to get your last points... but it will cost you.

I'm not sure it is even possible to finish Rachel first; not even sure if she can be finished anything but last, currently, but it sounds like a fun experiment. The influence gets from all but one of the teachers are extremely straightforward. For the last one, take as many girls as you can as far as you can.