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My spouse and I typically plan 3 to 3 1/2 hour legs, and we like to limit each flying day to 2 legs. We've done more than that, but it's tiring for both of us. We file and fly cross-country exclusively IFR, but do not challenge any weather. If I can't get there in two legs, we'll split it up into 2 travel days, and use up some of our hotel points to stay overnight somewhere. We sometimes refuel at non-towered airports, but try to refuel and remain overnight (RON) at towered airports. Normally, we like to travel on weekdays. So, if it was us, we'd pick Option #2, but make a FBO, hotel and car reservation where you plan to RON, say at Des Moines or Topeka or somewhere. By my quick math, you're looking at 11+30 flying time at 140 Kts average groundspeed, probably more realistic like 12+30 flying time including climb/descent and headwinds. So if it was me, I'd do a first-draft of a plan with something like
VKX-DAY (3+15), refuel, then DAY-PIA (2+30) and lunch, then PIA-DSM 2+00 (RON). The next day, we'd go DSM-LBF (3+00), refuel, then the final 1+30 push into Denver Metroplex (prefer CFO over APA).
Personally, I almost never go "direct destination" -- preferring to file/fly over or near major airports (just in case).
So it takes a lot longer than commercial air, and probably way more expensive, but 1000% more fun for both of us. I always take an extra day or two off work for these trips, to give ourselves an "out" if weather or maintenance tries to stop our progress (which it has, twice on one trip, even!). I think for us, the key is our flexibility--we don't ever plan something that means we absolutely HAVE to be at place X by time Y, and of course, we never travel without the all-important credit card which fixes a lot of issues! "The journey is part of the adventure!"
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