Need advice for rekindling my relationship with my father.

I’m 23 and live with my mom and dad. I love both of them to the moon and back, but my dad is very overwhelming. He’s loud, loves to rant, loves to be right, and such. He asks me the same catalog of yes or no questions since over a decade and says hi to me on average 4 times a day when i’m home, and he expects me to just keep answering, it really drains my energy. It pesters me, and I can see it annoys my mom too. It gets annoying to the point I try to not respond so he stops doing it, but no luck. Now it probably sounds like a simple conversation would fix this issue, but he gets hurt very easily. If I told him to stop and that it annoys me, he gives this puppy dog sad face and sad voice that makes me feel terrible. He gets along with other people fine, even my buddies, good conversation topics and all that. Except with family it’s like he doesn’t know how to interact. I’ve actually walked in on him one time crying by himself and him telling me no one talks to him and I hugged him. He tells my friends he wishes I would talk to him, and that just angers me. His dad died when he was little so I understand he’s trying his best, but it’s like he doesn’t want anyone telling him how to be a dad. It’s eating at me because I feel terrible and don’t know if it’s his fault or mine. Any sort of advice would be much appreciated!

TLDR: My dad annoys me and my family with his constant pestering, and I feel bad for ignoring him / telling him to stop because he gets really sad. Need advice.