Now that the kiosks and online checkin will both give you connecting boarding passes when you initially check in, it doesn't seem like there is a need any longer for kiosks within the secured area. WN can probably make better use of them outside security near the traditional checkin area.

For the few cases (such as yours) where customers have 2 tickets or for whatever reason can't print a connecting boarding pass before their first flight, they probably figure any gate agent can handle it or some larger WN airports have customer service offices within the secured area.

In terms of security, I'm not clear on how WN moving its kiosks would affect security -- you still have to go thru TSA metal detectors etc. regardless of where WN's kiosks are located. ??? And there's no need for WN employees to be rude to people in those rare cases, unless it's a new crackdown on people maximizing flight segments and/or saving money from strange pricing (DTW-MDW is $39, MDW-TPA is $49, but DTW-MDW-TPA is $139, etc.).