Should I Retake the SAT??

I have taken the SAT twice

2090 (680 R, 720 M, 690 W)

2310 (730 R, 800 M, 780 W)

I am definitely happy with my 2nd score, and I would be fine sending that to colleges because I know it’s a great score. However, I know I can raise the CR score if I study over the summer and take it again in October. Would that be worth it? How much of an increase in my reading score would I need to see for it to make a difference?

I assume you’re applying to an ivy, and to be frank, anything above the 2250-2300 is good enough. If I were you, I would apply EA or ED to wherever your top schools are as soon as the application opens. Best of luck.