I would say no on the card from the baby. That's pursuing.
Hiring someone is a tough one. On one hand it just part of you being independent and getting a life. On the other hand I'll bet a dollar that he'll be hurt and feel rejected. I guess I'd say have them done, but prepare to have him "come at you" in conversation afterward. You want to prepare yourself with a very detached, non-blaming, non-accusatory response.
Finally, read through SSM as soon as you can. I'm working through a SSM. I can't begin to explain to you want it does. Don't be frozen by the past after read it, just move forward with the learning.
