So, after having my old PW3 laying around unused for over a year now (bought the latest Oasis last year), I've decided to jailbreak it the hard way.
Soldering the pins went relatively straightforward - the hardest part was removing the front plate of the device without ruining the glue strips.
However since I've had the serial port wired up, for some reason the Kindle won't boot completely properly in regular mode. It starts up, but during the boot animation (the bar filling) the screensaver flickers in for a moment or two, before settling on it permanently. Through the serial port I can see it boots properly, and after doing the first step of the jailbreak (removing the root user password from the "regular" system partition), I can log in and play around. The device does not respond to the power button (apart from the 15 second long press to cut the battery), and after some time, sending data to the Kindle through the serial port also hangs. It is not frozen, since if I e.g. long press the power button until it reboots, or connect a power supply, I can see logs coming through - but entering any data is not possible.
At first I thought it's a hardware fault, however diag mode does not produce this effect. In diag mode, everything works as intended, the serial port does not freeze, and I do not get locked out at any point.
What could have gone wrong? I've literally didn't even touch the main OS partition at first, the only change that happened between it working and suddenly producing the above effect is the two pins being soldered to two freestanding (insulated) wires. They are not crossed - otherwise I wouldn't get any output through my adapter.
And what could be done? I was thinking about using the recovery mode that is prompted during boot, which offers to flash a *.bin file from internal storage. Since my PW3 is on a relatively old(ish) firmware - 5.12.1 if I recall correctly - I could flash a somewhat newer, but still not the latest firmware.