Asking AIKO about Kurt will lead to mention of the Valkyrie program. But you may need to lean on his past with Bob and Mr. Bergmeister to get Kurt to agree to the initial enhancements.
Dialogue will reflect if you've experienced the Kurt threeway or not.
Requirements:
Complete the Bob recruitment
Own a maid uniform
After you complete Bob's recruitment, visit him at work.
Talk with Bob about getting Kurt to your side. He will give his thoughts and point out how "by the book" Kurt has always been.
Tell Bob about the Valkyrie program to continue.
After explaining the program, Bob will agree to lend a hand as soon as you make arrangements.
After talking with Bob, find Kurt at the maid cafe.
After you mention Mr. Bergmeister, Kurt will be ready to help.
His dialogue reflects your relationship with Kurt and any previous events you, him, and Bob experienced.
Bob will then show up and ask for Kurt's help and mention getting military grade upgrades at the chop shop.
You, Bob, and Kurt will then go to the body shop to get Kurt's enhancements installed.
If you aren't AIKO's avatar, Bob will put you to "work" while you wait.
The surgeon will come in and tell you to come in dressed in a maid uniform so Kurt can focus while the surgeons set his personality.
After performing for Kurt, the surgery will be complete. You now have a powerful soldier to help you take on SISSI.