Tape and Pressure Technique
The last serial jailbreak I did involved no soldering as well (after 1 botched solder job and 3 successful ones). I just used my usual 3 wires off a floppy ribbon connector (spacing is just right) attached to my 1.8v serial cable. I aligned the 3 stripped wire ends over the TX, RX, Ground pads, put a piece of electrical tape over them. While I typed in the commands with my right hand, I used a flat blade screwdriver in my left to hold firm pressure on the the wires over the contact points. This is a bit tricky but you can tell when there's a problem because you get garage characters on the screen. Since my standard procedure is to flash back to 5.4.0 (I have PW2 2gb models -- DO NOT do this on 4gb models), I can do the two dds over serial then upgrade firmware forward to later versions the non-serial way. This is the fastest method I've used so far and there's no physical changes to the board.
Two tips: clean the pads well and use freshly stripped floppy connector.
Lesson: good old serial interfaces were really robust (and slow). They didn't have to deal with crosstalk and other issues affecting modern high speed interfaces like usb and ethernet. Basically if you can complete the circuit, it works.
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