It will likely of be little comfort, but it seems that you're not alone... Serial Port selected disconnects after upload. Given that this appears to be a multi platform issue and not specifically an rPi issue, you might have better luck on the Arduino forum.
The tty name changes because it gets re-enumerated by the kernel when another program is already "owning" it (it can be the serial monitor or the uploader).
The problem here is about the port disappearance; it could be related with the exact FTDI model or drivers in use, since the IDE asserts DTR at serial monitor open (to trigger a reboot on boards like UNO/Nano etc) and this could have some effect on your FTDI addapter (namely, it could restart if its DTR line is connected to some other rail). Selecting the "generic" module should disable this behaviour (see https://github.com/esp8266/Arduino/blob ... ds.txt#L25)
Updating boards.txt has solved my problem with open SM/port goes away, selecting port make SM go away.
However I'm still not getting any any comm when running a -01 chip. With the same (wiring wise) breadboard SM works with a -12 chip. So can anyone get SM to work with a -01 chip?