Dear Ed,
1) I've talked with our Types developer. It's problem with upload dir and normalization file name. Types started using only date structured uploads directory, example: wp-content/uploads/2014/01
This change was made to make it work right with WPTotalCache plugin (CDN storage). There are some fixes in trunk for image storing, but we think it won't be able to use wp-content/uploads/gravity_forms/ directory.
As it is a known issue, I've just added your ticket to the item on our to do list. Thank you for your understanding.
2) Please enable the debugging mode and let me know the error that might appear: wp-types.com/documentation/user-guides/debugging-types-and-views
Also try to test it without any extra plugins enabled and choosing a default wordpress theme.
