OK. I now have some experience with iBank. After hours of trying to get it to import all of my Quicken accounts and getting it hooked up to my various investment houses, I have given up on it. I give iBank chat help high marks. They were just unable to solve my problem.
The first problem is when you import the Quicken Essentials file, none of the investments are included. The meaning of this is, if your investment firm supports Direct Connection, you can hook up to the institution with login and password and download your portfolio into iBank. If it doesn't you're likely out of luck. I have an account with TIAA-CREF. They only support the export of a .qfx file for update to Quicken. This is a 120 day file of transactions, but it does not contain (or cannot be successfully imported into iBank) the current holdings, so there is not way short of entering every single stock and mutual fund and bond into iBank manually.
I finally gave up after two weeks. I am going to attack one of the other programs. I previously gave up on SEE and Money Financial, but I'll revisit. I can't even recall why I gave up. Already for the time I put into iBank I would have been better off sticking with Quicken Essentials. It's crippled compared to Quicken for Windows, but it's not bad and it does support category classes, something iBank does not.