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has anyone been successful in getting an auto loan with high debt to income ratio but proof that you're enrolled in IBR?

Yes, just got an auto loan a couple months ago. I was approved through a couple different credit unions. Nobody asked for proof of IBR. It's easy to get an auto loan, the issue is at what rate. Despite high DTI ratio, I qualified for the lowest rate at the two places I applied to (1.99%) since I have an excellent credit score.

Hell, I bought a $430,000 house and owe nearly $300,000 in law school loans. And I already had a mortgage on another house.

My credit score shot through the roof between my first year of law school and the summer after law school when I bought my first car. I asked the financing agent at the dealership how the hell my credit could be so high when I had 260k in loans. He said it's because having the loans actually adds to your credit score. I think the logic for credit-scoring agencies is that if someone trusted you enough to give you hundreds of thousands in loans, you must be a good borrower.

The amount you owe on fixed items like loans or mortgages don't affect the ratio component of your credit score. I'm right around 800 even though I owe:

1. More than I took out in student loans - around $296K right now;
2. $393,000 of my $430,000 house;
3. $94,000 of my $140,000 house (probably underwater at this point - I bought it in 2005).

The only negative it ever notes is my revolving credit usage, which is around 18-21 percent, give or take.