Subscription manager migration

So I have started moving my 50 servers from Classic to Subscription Management. Thing is they don't beleive they have any products installed. I can't beleive how hard RedHat is making this for me. I am now on with support and it is taking 20 minutes to get started.

Is there really no way to generate .pem files? How come it works for new installs? Is there a reason my old servers that had different SKU's can't figure out they are running RHEL 5?

At this point if feels like RedHat is a waste of time and money.