I've only been birding a couple years and live in NW Iowa rather than the NE, where you'd be heading. I've actually seen very few of the species you have listed. But hey, you'll be pretty close to the Mississippi and I'm sure there's more traffic there than over here on the other end of the state.
Are you planning to travel around the state for your birding or will you be staying around Decorah? I think you'd see a lot more birds if you were here in May.
We see a lot of Woodcock here in the spring, only heard one this past fall. I think Dickcissels are likely to have moved out by then (Sept). Empidonax flycatchers I usually just throw up my hands so I can't help you there, next year I have a goal to pin them down though. I'm always on the lookout for sparrows, especially the ones you listed. Caught a brief look at what I think was a sharp-tailed during migration this spring but can't be sure. Most of my time out walking around is in the few prairies left around here and I haven't come across them. Whip-poor-will I've heard of being spotted closer to the Mississippi. Greater Prairie Chicken, I believe the only population in the state is in the south central portion, same for the Kite.
I think the winter passerines you listed would be a real long shot in January, let alone sept. Doesn't look like the Black crested titmouse gets close to us, ever. Can't help with the water birds.
The link in the other response was a good one. Hopefully you can find someone in the area more experienced than I to give you some specific advice.
If you'll be traveling the state and find yourself in the NW portion (Estherville) I'd be happy to show you around the area. We have a couple decent (but small) prairies left, a lot of sloughs, and a couple bigger lakes nearby that , from what I've heard, can provide some interesting (for us) waterfowl during migrations.