Good suggestions, Ron. I actually have a whole set of songs about cities and states (New York, New York, I Left My Heart In San Fransisco, Chicago, Do You Know What It Means To Miss New Orleans, Abilene, etc., etc.) These are mostly "standards", but for some audiences I do include the Sparks "Denver" song (which he stole from "Acres of Clams" by the way.) And I do like "East Of Denver" - haven't done it in awhile because I'm afraid of lightning striking me - I wrote another verse to it, something that Mr. Stewart berated me for.
As for the patriotic medley, I probably should look into "Power and Glory" - I have a personal aversion to it though because of the people I associate with the song. As for cutting "God Bless America" - nah - it works. And it really is quite different than "God Bless The USA." It's one of those American classics that stands on it's own.
I've never been too big on sea chanties, so I probably won't go there. My Green medley went over pretty well last night. It had an energy of building excitement to it and the audience responded to each song in order with - oh, yeah - great song. The rest of the night went well too. I solved my last song issue by closing the first set with a medley of "MTA", "Tom Dooley" and "Tijuana Jail". Second set ended with my railroad medley, closing with "Orange Blossom Special." All in all, it was a fun gig. Nice crowd and very nice venue. They asked me back, which is the highest compliment.