Things went pretty smooth on the right port. I had 1 RDP disconnect that lasted about 2 seconds max. No other RDP session indicated the disconnect and the screens did not go black. I ran a little over a day with some staff interruptions so I may have missed it if it did happen
Preparing the laptop for the end user I disconnected everything, powered off everything, removed the USB 3.0 cable, connected a USB 2.0 cable with ferrite cores between the dock and laptop USB instead. It is currently connected to the left port which is notorious for issues. I briefly saw 2 USB indicators in the notification area that were going to tell me my device could preform faster. Now its time to use it and see if it goes all messed up.
Dell XPS 13 Intel USB
USB 2.0 cable (left USB SS 3.0 with powershare)
Kensington SD3500v (main USB SS 3.0 port)
Items connected to the SD3500V ports
Plantronics headset plugged into headphone and mic ports
USB 2.0 cable to dell usb port 2208wfp
Ethernet cat 6 to 1gig switch
DVI to VGA adapter to first 2208wfp (1680 x 1050)
hdmi to dvi adapter to second 2208wfp (adapter on dvi of 2208wfp) (1680 x 1050)
external power
items connect to the 2208wfp usb port
dell usb keyboard
dell usb mouse