<p>Any transfer after, obviously, freshman year will be difficult. Relative to the other options, being a postgraduate or new sophomore is easiest, as postgraduates are just that, postgraduates, and new sophomores are typically admitted all the time, so classes grow quite a bit. Junior year is often also the most difficult year of high school anywhere but particularly at an elite and academic boarding school. Visiting colleges, planning a stressful senior year, adding to your extracurriculars, taking APs, maybe studying abroad, this all sounds hectic to manage on top of a new environment in which you have to live, work, and play. It might be worth it to think about repeating sophomore year and thinking about those advantages- possible easier admittance, an extra year at school, more adjustment time, etc.</p>