I have to say, I liked the edition of the small font. My eyes aren't as they use to be, and it's been years since I played a game like this. I tried out both versions, and I have to say I'm liking the way the small font looks more. I had a issue with the music disappearing on me during the breakfast scene, but I couldn't replicate the issue so I'm thinking it was on my side.
I did run into another small issue:
A picture flashed of the teacher for a few seconds, and went black. This is day 2, Tuesday. English class. I was on this screen for a few minutes because I was writing down a note for the review. It's not something that is game breaking or even noticeable on usual game play, but all the same I felt I should tell you just in case it does become something.
I was honestly very surprised you did this in ren'py, it never crossed my mind it was possible to do old school games in that program, but I'm impressed. It shows experience in redoing the UI and front end.
It reminded me a lot about school. Freddie is just focusing on the day to day, and working with the different relationships around him. The disappointment of bad grades, not being able to reach someone, and the uncertainty of not know what to do.
(I tell you, I failed most of the questions off the bat, it made me slow down more and reread everything)
I really enjoyed it, I'm still playing it, trying out all the options and routes. I really want to see everyone's backstory and make Freddie do good. The fact you had all these options done, and this much different scenes is impressive.
My last suggestion is that the icons were hard to tell what they were. It took me awhile to realize it was a S and L, and that there was a options button, I just kept clicking esc key. I would set up a tutorial in the description or in game if you don't want to change your icons. Press right click to save, etc, etc.
Wonderful job though! I look forward to seeing what else you do!