You need to learn how to read, because all your questions have been asked and answered on this thread, not once, not twice, BUT SEVERAL TIMES. But if you're too lazy to look for them:
1. You need to do it SEVERAL TIMES, NOT ONCE. AND you need to give the work to Elena FIRST, get rewards from her at bath room, 22:00 on Wednesday, BEFORE turning it to Bill.
2. You have to do the above, while also spy on Annie on Sundays, at several hours (10 at her room, 12 at Bill's room, 21 and 23 at her room), until you find Bill forcing a bj on her. After you intervene the first time, Bill will show up, offer you money for you to back off, you need to take it. Then you need to repeat the process until Bill force a bj on Annie a second time, but this time, instead of intervening, you go tell Elena so she catches them. After which, she'll show up at your room early morning and one of the 2 icons will light up with hint. It will basically tells you to wait for a third forced bj and take a picture to show to Elena. Then, you have to get Elena to give you bj 6 times: massage session on Wednesday (replace the masseur option at 14, and do the session at 15) to start off, get reward for Icloud hack Wednesday at 22, at breakfast on Saturday (drop the fork), Monday morning massage (9 at bathroom, need to successfully massage her in bathtub pretending as Bill first), Tuesday at the pool at 15 (ask for titfuck), and then lastly, Wednesday at 14, offer to rub sun tan oil on her on the balcony, don't pull your dick out but choose continue and then ask to take off your clothes for rewards. After all 6 bjs, the last icon will light up.
3. They are fantasies during "Help with homework". Probably the earlier 2, so redo that and choose the earlier fantasize option. You need to repeat it a few times to reach the last scene for each of them.
4. It's likely a bug. If you have vistited Annie several times at 23 and do everything you can there, you have already finished it. If you want it light up, just go to save file, find a line that say eventAnniesleep, and change the value from 5 to 4.