When I enter Rachel's room at 10 she is always sleeping.
The fact that Rachel is sleeping is very important. Thanks, this is greatly helpful information. It tells me that you didn't complete the First Milestone (Mr. Elwell stepping in). Your screenshot also confirms this, which is great.
Now I know this was the reason why you were stuck on this path. OK, so you need to do the following to unlock the 3rd and 4th star.
What you need to do is use the old unlock for the Aunt event for a little bit still.
Go at midnight to the pool. When Rachel is swimming put the sleeping pills in her drink. If you don't have this quest talk to Susan. You did this quest several times before (based on your screenshot) but seems like you skipped over some of the dialogue or forgot so just try to fully repeat the steps you did previously.
"Do you need my skills" or something like that From Susan to start the quest ---> Midnight at the pool, sleeping pill Rachel's drink --->go to Rachel's room at 01:00 after pills take effect, disable her alarm clock ---> Tell Susan of your success before Lunch -----> Enter Rachel's room at 20:00 when there is a session between her and Susan.
Once you generate a Session between Rachel and Susan: you will need to pick the "kneeling contest" and win the kneeling contest (disable femdom in the help window, unless you are really interested in the MC losing the contest scene, but then your progression might be a little longer.) Once you win the kneeling contest against Rachel twice you will need to pick both options. Have her masturbate in front of you and spank her.
Once you do all this you will have to do a phone call with Mr. Elwell, your uncle who will reveal some information.
After all this is complete go back to Rachel's room at 22:00 and enter see if anything is different.
Sorry if my description is not really clear you can probably find better ones in the thread. The important point is before the milestone you will need to sleeping pill Rachel, and you somehow missed a step in that chain and forgot about it. (Took the quest didn't complete it. Completed it didn't turn it in to Susan before Lunch something like that). So just try to do whatever you did when you first unlocked Aunt Makes mistakes, but pick the kneeling contest and win it and pick the appropriate reward to unlock the first milestone stars.