Interested, make an offer of hourly rate. Available this thursday, friday for most of day in GMT-4.
I am fairly skilled with Java,
15K user on Stack Overflow with focus in Java.
I am not skilled with Jpype but can read up on it before helping you. In a worst-case scenario if something doesn't work through JPype, I can do it on the Java side and have Jpype invoke that, so I am certain in my ability to handle any issues.
It would be good to know which library/libraries you have in question.
Skype is probably not workable (I use Linux and haven't gotten Skype working reliably), but IRC (private live message, or private channel) should be fine.