Can someone help me?

Context: There is a friend of mine that invited me to go out for dinner with me. We went to the same boarding school together two years ago. Our first year at the boarding school, told him that I had a crush on him but he told him that he was not interested. However, even though that happened, we were still good friends during our second year too. Furthermore, yesterday, I was in the city where his university is located and I decided to text him to ask if he wanted to go for a little reunion. We went out and he literally paid for everything; he paid for my uber to go to the restaurant to meet him and to go back home, and he paid for the restaurant bill.

He told that he was paying for everything because it is his city and I don't have to pay for anything. Then I told him that he should come to visit me at my place so I can also put things on me. He told me that he will still pay for everything because my city will become his city

First question is Do you think that he has feelings for me? Because we weren't really close during our time at the boarding school but he still paid for everything and became available to meet me for by time there. He did flirt a little bit but he wasn't obvious because he is shy. He would only say things like "you have changed a lot since the last time I saw you" and "i'm glad to be the first one to take you out then" when I told him that he is the first guy taking me on a date and acknowledging that it is a date.

Second question: I may go back to his city in December. Should I text him to ask if I can stay a few days at his place? I'm think of asking that because he told me that if I was staying there for more time he would invite me to go have some food made by him at his place. Also, because the place that I stay there is far from his place so I want to be able to go out with him without limitations.

Updates
7 mo
Thank for the answers!! I don't know if I would be able to date him, I want to. But I don't feel like a long distance relationship would work between us so I guess my time there will be just to get to know him more and try to avoid any sexual interaction since I feel like things with him may work later. What do y'all think?
Can someone help me?
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