I've done some Wiresharking and see that it simply makes requests and sits there for a couple minutes before getting the SSL change cipher spec handshake at which point it connects. I've also done more testing and have found that A) this only affects IE, B) it is only reproducible via IE using either the public IP or URL, C) internal load balanced IP addresses are not affected and D) no other browser exhibits this behavior.
So, Firefox and Chrome both will accept and follow the 302 HTTP redirect to HTTPS immediately with no lag using either the public IP or URL. IE will instantly redirect to HTTPS only when using the internal load balancer IP address or by typing in
https://url. Otherwise, browser makes a successful HTTP request to Wingate -> Wingate gets '302 moved temporarily' -> browser spins for 2 minutes with no errors and then displays the HTTPS website
This behavior is only when going through Wingate and only with IE. So, does IE have some issue with Wingate? Really strange.