I think your machine is suffering from what I the "pre-Vista and Windows 7 blues". Software drives a lot of hardware upgrades and unfortunately, the older software does not run on the new computer operating system formats. You may have someone trying to upgrade a port but it probably is not going to really solve your software issues. I found that after a long philosophical discussion with my dealer that purchasing a stand alone embroidery unit was by far cheaper (in the long run) than spending the money for a top-of-the-line sewing machine. I have a great sewing machine (so do you). You might want to look into options like this before you try messing with your machine because it sounds more like even if you fix the port you will still have the 3-D to 5-D issues.
You could go old school like I like a lot better (much of the time but then I don't make embroidered quilts, etc). My embroidery is free-motion (zig-zag or straight stitch and dropped feed dogs and I'm good to go).