@Mwfan1921 thanks for the feedback. I was always under the impression that you had to tell colleges you were thinking of transferring into why you want to leave your current institution without completely knocking it down. What I’ve found online for some colleges is that they seem to be asking this. For example, UChicago seems to ask 3 essays: Why UC, Why Transfer, and the personal prompt. How would a ‘Why Chicago essay’ and a ‘Why transfer’ essay differs in that case?
I have indeed reached out regarding possible transfers for the fall of 2020, and unfortunately nowhere seems to be accepting applications anymore. Vanderbilt technically has a rolling admissions policy, but talking to their AO they seem to have filled their entire transfer class at this point.