People

This is a lot more realistic in terms of regression stories. Aeloc goes back in time, knowing his mistakes, but he is still him, and he is still too trusting, too kind and too forgiving (which is why he doesn't see that cloff is someone he should hate, to him cloff is still someone who he needs forgiveness from). He is making different investments probably, but they are still bad ones, as he is too soft-hearted, he is an idealistic and artistic person. Its not like he knew of every major event happening while living on the streets, and not like he'd learn finances and management magically just coz he reincarnated/regressed.

This is a pet peeve of mine, how the characters somehow know every correct choice after going back in time, but had room temperature IQ before that. If you had the analytical and deduction skills, why didn't you use them in the previous life? Aeloc simply doesn't have the skills to manage well, to finance prudently etc, while being in charge of a fortune too great not to attract cheats and scammers. In the previous life it was Cloff who took advantage coz he had a vendetta against him, in this life it is other loved ones. Bear in mind that none of Aeloc's loved ones came to his rescue even in the first timeline.

Aeloc's only issue was that he has had a lot of noble pride beaten into him by his father. He sees a show of force and grandeur as the standard for nobles, so he incessantly holds the tea parties, and also why he saw it fit to try to scare raphael off in the first timeline.