Unsure about college pathway

Hey everyone, I'm a senior in High School and am in a predicament regarding my college decisions. I was accepted into a few semi-targets (USC, Emory, UMich Econ), along with a couple safety schools (Basically a full ride at UIUC), but I also have a transfer option (guaranteed transfer) to Cornell. I was really upset with my results and I kinda attribute it to being at a super sweaty high school (Stuy), but I want to transfer to a top target. 

My plan right now is to go to UIUC, get a 4.0, and apply to transfer at UChicago (ED), Penn, Brown, Dartmouth, Columbia, and Duke, and if I don't get into any, I'd probably just go to Cornell with the transfer option (which I'm not looking forward to as the Transfer option is not for Dyson or CAS - I know that recruiting is practically the same everywhere at Cornell but I also just don't like Cornell very much in comparison to the other schools on my transfer list). However, I have a few concerns with my plan that I'm hoping to get addressed: 

- When I transfer, how will IB recruiting work, will I have to grind for a sophomore summer internship in sophomore fall, and a junior summer internship in sophomore spring?

- Will I be at a major disadvantage compared to the non-transfers in terms of recruiting?

- My dream school is UChicago, and the transfer ED acceptance rate is around 8-10%, what will make me stand out the most on my transfer app to UChicago compared to other applicants, and additionally, do you guys have any tips for me to transfer into any of the other schools I mentioned above? 

P.S - please don't discourage me about applying to transfer to UChi (I know the social scene sucks and I don't really mind)