I don't get why he quit high school like that; I'm not sure if the real reason was given and I missed it or what (not the excuse he gives the school but his real motivation).

I don't get why he moved where he did and apparently spends his days bumming around and "helping out" despite saying he didn't want to be used for his money and how his friends all left when he ran out of cash. Everyone around obviously knows he has money and he gives it away all over the place. He's still being used for his money, (they're just strangers/ neighbors now instead of friends).

no matter how good he feels about helping others, he basically put himself in the same situation he complained about and hated in the first place. I think I wouldn't care otherwise but the author spent so much time talking about how he regretted it in his first life that it makes this decision/action questionable.

For starters why MC helps people unrelated to him - he do it to feel good, so thouse people will not become someone like him in original time line. It's called helping yourself trought others, psychotherapy if short. Why drop out of school, do this or not doing that? Do you know what goal MC have in the first place? Game? Be a good boy? Become rich? Revenge on his friend? He want to find the devil to make a contract to return again, but 15 days earlier. He just want a normal life with parents... ~Fin.