I've decided to make a thread so that all people who accomplished certain or all Trainz milestones can place them here. I'll start off by posting mine.
Just pick a train and drive but it has to be in session mode and YOU have to guide it. The A.I. can't be operating it even without commands. Once you tell to "drive" it no longer counts towards driving experience. Also don't do anything to force a database repair as it'll reset EVERYTHING. At least in TS12.