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From a user experience perspective what would be the most intuitive layout for checkboxes and labels on this form?

enter image description here

(Click here for full size image.)

What would you guys think is the best way to display the label and checkbox together because of the fluctuating width of the labels? And from an objective view, what would be wrong with this approach?

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Is it fluid? I mean, how does it display on smaller screens? – A.L Feb 12 '14 at 14:11
No its not fluid or responsive. – RaVen Feb 12 '14 at 14:11
Just a comment: try to align the fields to the left to reduce the distance needed to fill the form. For example, you have to go far away to check Designated. – A.L Feb 12 '14 at 14:12
Do you target use on mobile devices? – A.L Feb 12 '14 at 14:12
I'm affraid it's almost illegible. Using checkboxes in this form never works for me, so I think it should be - definitely - switched to vertical. The thing is that it's hard to fully understand the purpose of this form for me, could you provide more details? – Dominik Oslizlo Feb 12 '14 at 14:12

I think vertical layout will be far better in this case, and you should also group fields.

Note, that I am not sure if I grouped the fields correctly, as I don't know the bigger picture of the purpose of this form (so please correct me if I made mistake) but here is an example how it should be dealt with (at least pattern-wise):

enter image description here

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This looks neat. The layout needs to be horizontal, but do you agree that the checkboxes needs to be inline with the labels? – RaVen Feb 12 '14 at 18:35
Much cleaner, would suggest using 50% to increase readability and be consistent with the 30% directly below. – Mark Sloan Feb 12 '14 at 20:49
@RaVen - even if you finally decide to use horizontal layout, the options should be grouped somehow and checkboxes should be inline. – Dominik Oslizlo Feb 12 '14 at 22:43

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