The moisture question is a big one, and I'm not sure how well the NAM and GFS have a handle on it. As I've mentioned elsewhere, they seem to be in their summertime "crops transpiring like crazy" mode, which isn't quite realistic yet. Example: the GFS has been blowing 12-hour dewpoint forecasts pretty badly for the last couple days, and I'm 99% sure this is the reason. Another issue is that we currently have high pressure sitting in the Gulf of Mexico, which means weak winds. Weaker winds generally means the air mass takes longer to moisten, and the models won't handle that well, either. Granted, there don't look to be any big interruptions in the flow for the next little while (until GFS fantasyland), so once we can get the Gulf to moisten up, it should stay that way for a while.
I don't usually like "directional shear" when looking at hodographs. The reason is that what matters is not directional shear, but the curvature of the hodograph. So if you take all the points on a hodograph with good "directional shear" and shift them to the right by 10 or 20 m/s, you've got a wind profile that looks "straight", but actually has a lot of curvature to it. Granted, southwesterly surface winds in the plains carry other problems (dry air transport, lack of surface convergence, and others), but none of those have to do with the magnitude of the shear being felt by any storms that form.
One problem with capping in IA on Wednesday is that the best mid-level forcing for ascent is still to the southwest in KS and OK. Also, IA is in a region of height rises on both the GFS and NAM Wednesday afternoon. Height rises usually mean sinking air, which means more capping. Both models do remove the cap in the region of the triple point in northwest IA, but they also mix out the moisture, which means LCL heights will be pretty high, and that could get worse, depending on how the moisture forecasts verify. Lots of people like to target the triple point because the surface winds are usually backed there, but as you note, this assumes the moisture can get there!
Many of these issues will be at least somewhat alleviated on Thursday, so if I lived in IA, I'd keep an eye on Wednesday, but not plan to chase until Thursday.