There are some auto rewrite rules. Off the top of my head: numbers in the beginning are stripped, [pdf] or [video] can be added to the end, and one more I can't remember that gets stripped off beginning and can cause confusion.
A pdf link to "5 Reasons To Do Things" will be "Reasons To Do Things [pdf]" for example.
There was also an interesting article on assistive technology called "How Disabled People Use the Web", or something similar, which looked very silly with the "How" stripped.
Yes. And the algorithm is really incredibly stupid, but dang is opposed to even small improvements (like showing the changed title on submission beforehand, like the „x characters to long“ message).