As the OP did state he would be utilizing a VFD the minimum sized transformer capacity requirement would typically be 500 kVA. If the application did allow for ACTL starts then a larger capacity would be required - but there are thousands of VFDs at 500 hp that are powered through 500 kVA isolation transformers. You could in fact purchase a PF7000 or PF750 with as integrated transformer (step-up, step-down, whatever you need) & Rockwells initial sizing for 500 hp would be around 500-600 kVA for that. If the existing 480 transformer and gear have capacity for at least 500 kVA I would have zero problems with adding a 500 hp motor on a VFD if that was a pump type application. If it were a high torque app that required 150% (or more) torque for long periods like a big conveyor then I would use a 600 to 750 KVA isolation (or capacity need on existing). If you have to add additional transfomer capactity for this application I would price out all the requirements to see if you go PF7000 or PF750, it may surprise you. I have done as high as 700 hp on a 480 volt Rockwell 1336 Impact & have also done some 400 HP 4 kV PF7000's & last month a 400 hp 480 volt PF755 at the same location. The last time I checked the break-over from a total cost stand point was around 750-800 hp. Above that point 4 kV was cheaper, but it will vary depending on current copper costs.