Did you manage to solder wires to the pogo? I gave up and designed all packs with 14pins pre-wired now 
Yes, but I needed three attempts.
The first one was catastrophic. At the last pin I did solder a bridge between two pins which I could not separate anymore 
I have used too much solder overall.
The second attempt worked out but still not nice. Used less solder but still too much. I did the dumb mistake to use super glue afterwards on the pins. The isolation of the wires became brittle and after bending the isolation cracked.
The third attempt worked out great with no pain.
You need to put just a little bit solder on the pins and on the wires. Then add some solder to the tip of your iron and then first touch the pin and then push the wire between tip and pin. The pin will suck up the solder and then quickly remove the tip. It is important to not use too much solder.
I have used the small TS100 iron for this job.
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I forgot to mention one hack regarding soldering the pogo pins. That is probably the most important one.
Put the pogo pin on a steel plate. This way the magnets less likely catch your iron tip. It still happens if you are not careful but it happened like 2 times only during my third attempt. You could probably improve it further by taping down the pogo pin.