The easiest fix for now would be to make the post legs longer in your model.
The road tool can stick to a surface more easily as it is a 2d object (texture). This method would not work for 3d models, it would not be seamless.
Aside from modifying the model to bend (which could look very weird), I believe it is a part of environment design and model usability, if you wish to use different heights then that can also be modeled to look proper (low to high/high to low connector models).
If you are requesting a feature request, that is great and you can submit it officially to the Ideas page on our Answers section. Make sure to elaborate fully on what feature you want added and how you would ideally want it to work and why etc.