According to Transition you could put one of their switches at the head end and it would make out everything downline, including other switches up-linked. However, I don't think it will be 100% perfect and we haven't tested that extensively, though on our own inhouse one we do see some of the up-linked switches and their end points.
If the network is all Transition DMS models it should map correctly. I just can't say 100% because honestly while it's a nice feature, we don't rely on the maps that heavily yet as we rely on our own drawings. But having the maps is a great benefit to see if something changed or someone plugged in a foreign device, or seeing if something dropped off that was detected before.