It is sad to read that you were unable to make things happen for yourself and I certainly feel you were hard done by from some of your examples.
Being a product of the same education system, I can empathize. However, things have changed and I know of very different experiences. Although there exists rigidity in structure, administrators have become much more flexible and don't expect the same deference to authority that might have existed. Here are a couple of examples:
1) The story of how CS3216 got started in NUS is classic: http://www.comp.nus.edu.sg/~cs3216/
Students knew of the recently started Facebook class in Stanford and thought it was a great class to have in NUS as well. They wrote out a proposal for the class. They approached a few lecturers in the CS dept before finding one sympathetic to their needs. He committed to teaching the class. They refined the proposal with him. Then they went to the Dean and over a pizza, gave him a well thought-out proposal for the course, got his approval and further edited and refined it with his input. The course was implemented immediately the following semester. The pace of getting it done is definitely not usual but they did it.
2) From personal experience, having gone on a year-long exchange program, I came back to find that certain modules I had done overseas were not all mapped back, which left me having done extra modules which didn't count anywhere and still one short of graduating. I went to the relevant authorities - sent a bunch of emails and had face-to-face meetings. Initially, I was told by an administrator that it was impossible and I would have to do an extra semester. I smiled at the person and changed tack. I figured out ways that the school could map the modules I HAD done and approached someone who could approve that. Eventually, I got the module mapping accepted and I graduated without wasting an extra semester.
My takeaways:
1) Look at your problem from their point of view - the extra administration it would require etc. This will lead you to 2.
2) Don't just show up with a problem. Do your research and propose solutions to your problem. If you ease the thinking required by the relevant authority, it will help ease your approval process.
3) Don't take NO for an answer - especially if you think you're right. Change tacks if one approach does not work.
4) Communicating properly helps a lot. Always start with deference and build a relationship before presenting your problem and solutions. They'll find it a lot harder to turn you down.