I think a lot of the questions here are arising from what "pushing the envelope too hard" means in this post.
It doesn't mean "don't do good work."
It doesn't mean "don't improve yourself."
It doesn't mean "don't use new features."
What it means is this: If you're going to do something new, make sure to thoroughly understand the subject before you release your work. Do use the features that the engine provides to the maximum, but don't rely on quirks of behaviour that aren't documented and don't have a clear purpose. In any complex system, there will be edge cases where the interaction between several behaviours is not clearly defined. If you rely on such edge cases, you may be able to make the system do something that it's not designed to do- but you're also very, very likely to find that the edge cases have changed in the next product release, and your content will no longer work.
If you're unclear whether a specific behaviour is officially supported, then please ask us. Regardless of how much we improve the documentation, it's never possible to cover every combination of features in a system as complex as Trainz, so there will always be edge cases. Several of the N3V employees read the forums regularly, so if you make a thread asking about a specific feature, it will generally come to our attention.
The more you "go it alone", make use of functionality which isn't clearly spelled out as part of the official feature set, or try to do things that nobody else can do, the more likely it is that you're walking in this grey area and your content may break in a subsequent release of the game.
We're not saying "don't experiment", but if you find yourself uncertain (or if you're taking advice from someone who is experimenting with new techniques) then please do talk to us about it rather than just assuming that everything that happens to work now will definitely work in the future.
hth,
chris