Yun keeps freezing on usb upload. I have to plug it into my linux box, and upload from your FREE ide (that also supports nodeMCU), then it works fine from my chromebook...until it doesn't. Rinse and repeat. Please make this software worth the $1/month I pay for it.
Is there a specific sketch that causes issues? If so, could you please share it here?
Make sure you're not using the receive and transmit pins on your arduino. Generally I avoid using pins 1 & 2.
I've to get the same issue (my set-up is Chromebook+Nano).
A sketch was just 106% of memory as I've found the with Windows 10 Arduino IDE try. Chrome was not able to spot the issue.
So the trouble might be routed in the sketch size and board memory limitation.
All the best!