We had Cadillac plans at all three programs I was at (TY, residency, fellowship). It really helped lower our stress.
Our residency program had the best plan. $250 out of pocket max (I believe increased to $500 my last year). So it cost $250 to have a baby, regardless of complications, etc. and the women were ecstatic that breast pumps were covered.
Monthly premiums were low at all three programs. We felt well taken care of.
Yes, I would be upset too if I was forced onto a HDHP. Especially if the monthly premium didn’t go down much, and if the program wasn’t filling up the HSA fund for us.
My TY did have a retirement plan—unfortunately we weren’t vested until PGY4, so I didn’t get to keep any of the employer contributions (they put money in even if we didn’t)
I think one bottom line here is don’t do residency in NY…