(Specific to IITB, but might apply to other IITs too; may add more stuff later. Thanks to Antariksh for his input)
Culture
Apathy is an art form: Apathy can be in anything--towards academics, extra-curriculars, or life. 'Ditch' is a well-accepted reply for anything and everything. More often than not, it's an attempt to avoid owning up to failure. If you are cool enough, you can manage to act all cynical about it too.
It can be difficult to break into a club/group after sophie year.
Unlike another post, I don't think politics is that big an issue in IIT(B). Whatever politics we have is a natural outcome of the process and is simply meh in intensity and impact compared to what happens in many other colleges. Less is always desirable, but the status quo isn't very alarming.
Dishonesty: A general problem with India, of course, and also visible in IIT. Assignments, exams, what not. There's always some justification to get over the guilt (the assignment was useless; I already know the concepts so practising it 10 times is pointless, and so on). Some departments (such as CS) have managed to cultivate a culture (using what is essentially a stick approach) of reasonable honesty, at least with assignment submissions and the like. Most other departments are still the same.
Dishonesty is still OK, but the fact that it is celebrated rather than castigated is what makes it depressing. Not only is it OK for the whole class to copy the assignment from one guy, if this guy refuses to give it to them, he'd be branded as RG, which is a term you can throw at anyone who is less lazy than you. The whole concept of RGgiri, which is sometimes used for selfish students who actively try to screw you, is mostly reserved by the lazy to describe those that refuse to let them get away with it.
Valfis (valedictory function, profiles are written about everyone in 4th year and read out by their friends) are fairly interesting a concept but they are often overdone and extend far beyond what they were intended for. I don't quite understand the perverse pleasure of calling a girl repeatedly for someone's Valfi just so that she can sit through the experience feeling embarrassed and humiliated.
I'd defer to a blog post by Nithya Subramanian for her view:
"I don't know how I could have been so naive. Till two weeks ago, I honestly believed that a valfi was a time for memories and laughter, for honesty and closure. But this year as I watched closely for the first time, all my little illusions shattered one by one. I watched as people brought out the character flaws of their friends--things they disliked about each other but never had the courage to point out, disguised them clumsily as jokes and read them out into a microphone, on a stage, for all the world to hear. I watched as they spoke disrespectfully of friends and used words I had never heard of before and wish I could never hear again. I sat through many readings trying hard not to listen, too cowardly, too unsure, to get up and leave."
Of course, not all Valfis are like that:
"Of course valfis like I always imagined exist too. I like to think my own was one such. It was 9:30 am on a weekday morning and we had all been in our chiffon sarees and heavy jewelery for over 12 hours. We had spent the night reading, reminiscing, laughing, blushing and crying. The morning was quiet, the sun shone, but the terrace hadn't yet turned uncomfortably warm. I was surrounded by people I loved and respected. I couldn't have asked for more."
General male douchebaggery you can expect in a testosterone-rich environment. Naming pornographic videos shared on DC++ after the most popular girls, showing provocative videos to rile up the crowd during major events, etc.
Administration
Apart from minor things, most clerical work gets done pretty quickly compared to other government offices. Guest house bookings are a major annoyance. Sometimes they don't let you know about the (un)availability of accommodation till the very last minute.
Loads of pointless redundancy in many procedures, involving a lot of back-and forth across floors, desks and departments.
Professors tend to have supreme power, and often cannot be overridden even by the Dean, Academics. This is mostly good, but it often leaves a lot of scope of abuse. And abuse does happen at times.
Pointlessly paternal at times: LAN Ban, 80% Attendance Rule etc. are all examples of the system overreaching and failing.
Academics
Inadequate: The curriculum is reduced, yes, but leaves out important stuff. Humanities education is almost absent, barring a couple of courses. There aren't too many courses or course methodologies that would inculcate critical thinking, analysis and expression, argumentation and logic. We are so down into the 'objective' rabbit hole, that we have practically no course where people can practise some extent of technical or descriptive writing. Listen to an average IITian trying to argue about something and you'd notice lack of all the above. The fact that all this curriculum is decided by professors who are all engineers themselves often makes this a positive-feedback problem.
Infrastructure
Hostels: Standard stuff; almost everyone has to stay doubled up for their entire IIT stay; hostel infrastructure is often old and in bad shape. (Even the new hostels suffer from poor maintenance.)
Food: Again, standard fare. Messes are OK, but uninspiring. Most people grow bored of eating there in 1-2 years and then eating becomes a chore rather than something to be looked forward to. Not good.
No proper place for mixed groups to work together at night.
Lack of any proper counseling service: There exists a counselor, but she sits opposite the office of the Dean of Students Affairs (DoSA). The reason given for this is that the counselor works in close association with the office of the Dean. No one seems to realize that the office is a very public location which is visited by countless students everyday and affords no privacy whatsoever.
I personally dislike the most about IIT/IITians, is an uncompromising ideology of regarding any lifestyle distinct from one’s own, as flawed.
PS: I am well aware that a comment like this is likely to spark debate, and in advance, will say that this outburst was probably a one-off thing and I will not be indulging in a rebuttal to a rebuttal to this comment, ostensibly, becoming a practitioner of the one IITian aspect I hate.
