How do I get through to him?

So my fiancé and I have been together for 5 years, and we have only been engaged about 8 months. Our son is 5 months and he is our first. My fiancé was/is my best friend and has been before we even started dating. We met right out of high school and he used to be a player, and he was one of those guys I connected with on an emotional level, because he had a lot of hurt and depression. I think I liked guys in high school that were hurting like I was and I liked taking care of him and being there for him. I really enjoyed helping him and hearing about the things that bothered him, and giving him advice. But since we’ve had a baby I honestly feel like I’m taking care of everyone around me and I’m not being taken care of. He supports us financially and he definitely loves me and our son and it is his life, and you can tell it is. But its just little things that bother me, like we never finished college and he says he wants a career so we can buy a house instead of renting and so he can provide a better life for us but then he never looks into school or anything. I have to push him for literally everything. I have to push him to go to the doctor and figure out his work insurance, and to fix family relationship problems. And it’s starting to get to me because I don’t want to be the dominant one. I want to feel taken care of. He is very sensitive, like I said I liked that before now not so much. I love him with all my heart but I don’t know how to get through to him without hurting his feelings. He helps me as much as he can with the baby and house work and works full time so I don’t know if I’m asking for too much. I feel like we should do counseling but I’m not sure if that’s a bad sign.