In my experience, when someone is interested in you, they make a lot more effort to talk to you and get together. It sounds like he doesn't care all that much, to be honest. If it takes this much work just to get together for the first time, it's not going to feel like a smooth connection. If you feel like you have to force a meeting, or if you question yourself on when to text them, or reply to a message, then something is amiss and it might be a good idea to move on. You have a lot going for you right now, so it's probably a good idea to focus on people who make more of an effort to be around you. It's not fun when it feels like pulling teeth to get someone to go out with you.
"Caring is not an advantage."