Hmm, do you have Python installed and which version of Python is it? I tested Tiled without having Python installed and with having Python 3.7 installed, but maybe this problem occurs when Python is installed but it’s not version 3.7.
Hmm, we need to get this fixed, but if it crashes instead of just failing to load the Python plugin then I think this may not be so easy. Do you need both 3.6 and 3.7 installed? Does it help to deinstall 3.6?
In any case, you can work it around locally by just deleting the “plugins\tiled\python.dll” file, as long as you don’t need Python plugins for Tiled to work.
It sounds like you should try uninstalling all versions of Tiled and installing new. I’ve never heard of Tiled not starting at all without error message.
If the problem persists, it would be nice if you could try compiling Tiled yourself and running it in a debugger, which may shed some light on what is going wrong.