#1 - Please put the wording "for Governor" below the wave of the flag in the design. #2, #3 - I like your idea of stylizing the H into a logo, the clien feels that this particular way is just to complicated. Is there any other way you could do the H that was political looking but simpler?
Wyoming's unoffical state logo is a cowboy on a bucking horse (known as the "steamboat") Also Wyoming has tons of wildlife such as deer, elk, bears, EAGLES. Wyoming also has the Snowy Range Mountain range running through it. Maybe this would help with some ideas.