So after running through various solutions to the Kick Harness issue on the I/O, I decided the fault is the I/O itself so it should be the subject to the modification.
I used my trusty dremel and went all dentistry on the header. Thankfully the quality of the plastic was friendly with friction and allowed some bits of it shaved off without melting or cracking. Now the Kick Harness is held (by friction) into the header.
Everything is fine now, the I/O is working like it should.
And all my toys are working like they should. All ended well this Friday, hope the same for the upcoming week.