I would submit that the biggest problem with your testing (and all the strange hub/non hub working oddities) is due to the nGear equipment rather than the IT support for USB hubs in general. I picked up a few different pieces of Ngear USB equipment to try out with the IT since they were relatively cheap and seemed like neat products (combination card reader/USB Hub... that's a neat idea); unfortunately I ran into all kinds of problems with them. I'm not sure if it's manufacturing, the choice of chips/firmware, etc, but they do not work properly.

For example, the USB hub gets detected as a Hub, and appears okay. Plug in one device to the first port and it shows up, things work fine. Plug in a device to the second port (even if it's a low power device like a keyboard) and the whole hub locks up, takes a dump and just dies. Worst part: it's a powered hub. The card reader that I got only appears as a single lun'd device, which contradicts everything I've ever encountered with other multi-card readers which tend to appear as 2 or three luns (i.e. one for the MMC/SD, one for the CF, one for the MemoryStick sort of thing).

Anyways, so I figured hey, maybe it's just those, it happens, some devices don't work fair enough. Other USB hubs and card readers (card readers connected to powered hubs of course) work. There does seem to be an issue with card readers and different card slots, but I have a feeling that has to do with the USB storage driver on the IT not expecting to have to try and mount/deal with anything beyond lun0 on a device.

Tried an NGear USB-Ethernet adapter, loaded the pegasys module that the supports the chipset, plug it in, check dmesg... detected the correct chipset, but pegasys module refuses to load and actually recognize it.

Alright, how about a USB-Serial adapter, should be straight forward as I know there are only a few chipsets out there. Again, grab an NGear one, plug it in... detected as pl2303 chip, no problems, but then pl2303.ko refuses to load. Now, this one seems to be due to the fact that pl2303 driver has been hard coded to only support specified manufacturer IDs, so fair enough the thing may work with a bit of hacking to the code, but overall the conclusion I came to was this:
Pay a few extra bucks and buy a decent product rather than getting the bottom dollar one and having to muck around with it.

That's just my experience though.