In some ways Roommates is a lot better: it starts with the writing - I simply like the light, joking tone of roommates better. The music of magic diary is between uninspired and annoying, here jack has chosen well the band who worked for roommates. And of course, Magic Diary does not support Linux64 even though RenPy should support it since ages. Update the library, Hanako!
However, Magic Diary has some good points as well. The first are the tests, where you need to apply the magic you learned to overcome obstacles. This system has two advantages: It makes the player feel like the student really learned something during the classes, something worthwhile. it also made the tests really like tests, and not just a date by which one needed to achieve a certain stat. And I enjoyed the challenge of finding out how to overcome the obstacle. With several ways how to succeed. Of course, in a magical college something like this is easier to implement, but still: Well done, Hanako.
The second point is the romancing. In roommates it is clear who is a possible partner, in Magic Diary this is less clear. And while Magic Diary seems to have the romance stats in the background as well, these are not shown. Thus it is harder to be sure who might be approached, and who not. This leads to a paradox: In Roommates I started to weigh every decision in terms of: will I get her if I do this. It took the focus a bit away from the (admittedly better) story. With Magic Diary I leaned back and experienced the story. Do something, see where it leads. Here it helped that the obvious love interests where males, and I do not really get much into pursuing males. So if I get him, interesting, if not, interesting too. Just enjoy the story while it unfolds. And the story took a turn which I did not expect. (sorry, Spoiler!)
If the length of the paragraphs gives a wrong impression: I still consider Roommates the better game, *very* subjectivly. However, the points where Magic Diary is better need a bit more explaining than a single sentence, and this is why the praise is so long.
PS: I would not have bought Magic Diary if it were not in the Humble Bundle, and if jack had not posted about it. So maybe I am still on topic
