
Her obsession with Cinderella route really puts me off ngl

It is something that needs to be thought about though and Mildred is just being cautious. If it truly was cinderella story, her and her daughter's lives are on the line (given how the original plot line went). And now that it isn'r following Cinderella, Mildred also is worried about the variables that could impact them with this plot change she didn't account for. I wouldn't say it is obsession but more so caution which is a good thing to have.

It's not obsession tho. On the first place Mildred is a reincarnated person. Just like any other FL she believes that she was in a story book. After discovering the similarities between Cinderella story, she believes that she is inside that story. Mildred is like those FL in other manhwas where they want to follow the plot.

In most turn back time stories, MC would make sure he or she does not make the same mistake again. I know he destined to be with that guy. But he should at least have sense to not fall for the same financial traps.

I don’t think he did that on purpose to see Klopp, he really just sucks with money and investments. After going through all of that torture, I wasn’t expecting much from Aelock.
It’s just my opinion but a lot of factors in Aelock’s loss of fortune in book 1, was orchestrated by Klopp. Klopp’s comment in the novel v2, really made me think ‘If just a few intelligent individual investors get together and try to scam you, Teiwind could be left with nothing.’ which did happen. So he probably knows what some to avoid, but it doesn’t mean he knows what to do.
He did try hiring a different advisor to help. He could have just hired Klopp right away, knowing how good he’ll be at this field. He really tried respecting his promise to Klopp, but was too desperate for a better agent. He knew poverty so he knows that if hirers another incompetent advisor, instead of going to Klopp it will be more of a loss for him. And by that time, everyone would have pointed him to Klopp’s direction. Derbyshire must have really talked him into hiring Klopp…

Thing is, Aeroc does remember what happened in his last life. He knows what he did to Klopp and Raphael was wrong and till the very end of his first life all he ever wanted was to make up for what he's done.
Yes, he made bad financial decisions in the first life as well as making bad life decisions; this resulted in the inadvertent murder of Raphael and Klopp's revenge by not only buy his estate but making him into an Omega in order to "take back" the baby/heir that was taken from him.
After being given a second chance, I'd sooner believe that he'd be more cautious in how he approaches Klopp and to leave him and Raphael alone. But as the end of the chapter showed, Aeroc still can't help but want to be around him because he still has feelings. And that is the risk Aeroc is taking.

I really think he asked more options before seeking Klopp’s help, because the timespan of the last meeting is almost a year.
Viscount Derbyshire who is like a close family to Aelock, who does care for him must have insisted on Klopp. That old man is really bothersome. (i know he didn’t help aelock during vol 1. But I think they sort of knew… and left Aelock to his own devices.)
Going back. This is how I understood Aelock’s mindset about his own return. He thought it was a dream, but as he realized that it was real, he internalized it as a chance for both Klopp and Raphael to be together. He still likes Klopp, but was just going to watch from afar, the sitting arrangement from the beginning, the omega woman was Aelock’s way to put a front that his with someone. When Klopp declined his invitation, he didn’t bother seeking him out anymore. But the financial troubles was really unavoidable, and since in the novel no one is as good as Klopp, well he’s stuck with Klopp.
So from avoiding Klopp, he tried just being cordial. If you read the novel, he really tries to help Klopp and Raphael at some point. I know even without the soiree things will progress normally, but someone else will be intervening…
Poor OG baby Lehir