I believe that there is an option to either "always automatically crossfade or never automatically crossfade".
Yeah, you're right about that. And I have that option ticked. But that only takes effect when you move a clip on top of another. What I'm talking about is close gap.
My workaround is just to have the fade options from the clip menu on a hotkey so I can get to it easy.
I was wrong that all other DAWs do it automatically though- some require the user to press 'x' to create fades etc. But some do it automatically which is very nice.
I just wish that the clip envelope was always visible when a clip is selected and that the waveform changed it's appearance in real time to reflect alteration made to the gain envelope. It's not long ago since fadeins and fadeouts weren't reflected on the waveform but Cakewalk got around to that. Strange they didn't fix this up at the same time.