Couple of pointers that may or may not be relevant:
First, one of the most spectacularly confusing issues can be dodgy USB leads. It looks ok, connects and is recognised as a drive, but - for example - you can completely fail to upload tracks with Garmin connect. If you are getting odd stuff happening - try another cable or three (pref good quality), try another USB socket, try making better contact in the Garmin or in the PC. When everything starts working ok you know you have found the problem.
As far as multiple names go, the Oregon will allow you to have two gmapsupp.img on both internal memory and the card, the limits with files are the os limits. But you will also probably already know that in gpx files there is a <name> tag that is the name the Garmin will display, so you can have file1.gpx & file2.gpx, with the name tag in both set to route0 and the Garmin will be perfectly happy.