Yes, I do think you have a shot at your top schools. Of course, there are no guarantees, but you won't be out of place applying to those schools, based on what I see in your profile. Your "apply and then apply to some more if needed" approach should work, given that at least three of those schools should notify you before most schools' Round 2 deadlines. Also think about Sloan and Yale, since they can also help place you in that kind of a finance job.
To answer your other questions:
1) Don't worry if you've never managed anyone! The kind of thing you described -- initiating projects, tackling problems no one else was willing to tackle, etc. -- are what admissions officers look for way more than how many people were under you on the org chart. Remember that they're used to evaluating young applicants (many of whom haven't yet officially managed anyone), so they're skilled in finding leadership traits beyond job titles.
2) Don't worry about this, either. Sure, all things being equal, it would be better to have a 3.98 from an Ivy League school, but the 3.98 is damn impressive, no matter what. And, what you've done is far more important than where you went. Don't waste any words in your essays explaining why you "only" went to a mid-size college in the Midwest.
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