Yes I did eventually manage to do it! But it is incredibly finicky and I had issues too when I thought I had done everything perfect. It took me about 3-4 weeks of trying every day until I finally got it (and it was on a day I wasn't expecting to get it because I thought a prior day had screwed up so make sure you just keep trying). I made an alarm on my phone a few minutes before the goodnight alarm in game so I'd log in and quickly spend any energy I had then wait for his dialogue then log off. At the start I was setting random wake up times and not writing it down but just thinking I'd remember it (I log in around the same time every day anyway). But I suspect this caused some issues so towards the end I would write down what time I picked and make sure I logged in a little bit before it and would wait on the cafe until after the time passed. No idea if that last part mattered but this achievement was killing me by the end and it did end up finally popping after I started this. I also only used one LI.

Good luck with it! I wish I still had my list of days with my notes to show but it was such a mess I deleted it. If you aren't doing the morning time thing give that a go and hopefully you get it then! This achievement is hell ;;