Should I transfer schools if...?

A $29,000 loan per year is way too much for anyone to handle. Definitely transfer. Going to medical school will only get you more loans. You might want to go to community college until you can transfer to an in-state university. Even though it might be an awesome school, it is not worth it to have that many loans - the average student doesn't even have $29,000 in student loans after they graduate so you definitely don't want to have that much after just one year.