Sigh.
First of all, plenty of people do precisely that. Many people here have done and do precisely that, including the person to whom I was originally responding to in this thread.
I generally take people at their word. When the majority of people here routinely assert that they are natal males who are straight straight straight men and that they just like to wear women's clothes because it's enjoyable and feels good to them, then I do not think that I am making an unreasonable assumption by saying that the majority of them are cisgender men who like to play dress up. You can argue with my tone, but I don't see the assumption that I'm making.
Please point me towards a broad claim that I've made that is not solidly based on what the people I'm describing in them have actually posted here, and I will consider your point.
Moreover, there is absolutely a benchmark for needing to transition. It's when not transitioning leads to unmanageable disruption, often an inexorable downward spiral, in the most fundamental aspects of your life, and the only way out of it is transition and living honestly. Alternatively, it's what a qualified diagnosis of a specified gender identity disorder (transexualism) used to mean, and really probably should still mean.