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This is interesting info! I have a bunch of different ones. Specifically this is trying a D1 (big style NodeMCU like board) and a few D1 Mini's. I think they are all using a CH340 chip for serial.
EDIT:
I'd like to confirm that the length of time doesn't matter. The garbage is reproduced for every connection regardless of how long I let it start up and stay idle.I can also confirm the board itself is not hung. I can get it to spit something out on a timeout which does happen even though the IDE says it is still "connecting".
I might have a look through the Web Terminal code tonight. My suspicion is that while it won't fix the issue directly, the IDE problem is likely the garbage tripping up the IDE and making it think it is still waiting for connection, even though in the background it is connected (as evidenced by the timeout test).
The "garbage" in the beginning is because the ESP8266's sends debug messages through the UART at a different baud rate. So that part is expected.
But (unless you intentionally pressed reset on the ESP when you tried to connect) I think something is not correct with the reset / Serial adapter circuit of your board. It should not start up when it's powered, and that garbage should long be gone by the time you connect to it.
This might be the reason why the web ide hangs: garbage sent first, and that "confuses" the IDE.
What board do you have?