Hope it's not too late but I wanted to chime in on the preference test. Overall I prefer #2 for the reasons others have said. The use of icons and larger clickable areas makes it more approachable. However, there are aspects of #1 that work better for me.
- Calendar Feature
The trip dates feature is hidden until I click the box (I would assume) and this keeps the overall space of the section smaller and I don't have to look at all that information when I am finished with the section. The calendar could appear as a popup or drop down. There are lots of existing code samples to make this interaction work for your developer.
- Medical Declarations
Finally, the boring stuff at the end about the medical declarations is easier for me to scan in option #1. It's left justified and in a bulleted list. Because this is critical to convey to the user, I'd want to make that as easy to review as possible.
Hope that helps!