That's so sweet. Aw, I'm so happy for you!

But.. I think you are overthinking it. Stop planning so much! Yes, plan where you're going to go on dates and things like that, but don't plan when you are going to kiss her. Those sort of things happen on their own. There is no need to plan for them, and that makes them even more special.
Don't worry so much! That's why guys trip or do foolish and funny things on date and embaress themsleves.. because they are so nervous about doing the right thing.
Just take it slow and if the moment feels right, kiss her.
You can break the ice by maybe kissing her on the cheek like you said or on her forehead or something sweet like that. That way, you have physical contact and you'll feel much more comfortable and not so nervous when you do kiss.

To keep the relationship going.. well, I guess make sure you always communicate with each other. Always make sure you guys are on the same page. Make sure that you are always there for her and you support her, which I'm sure you do already. Keep it exciting and try new things together, it'll keep you from getting bored with each other if it's not always the same old thing.

Good luck!