Logging in with multiple CC accounts, personal and enterprise

Question

I need to be logged in to two CC accounts with two different email addresses at once, one is my preexisting personal and the other is a new enterprise.
One is used for Typekit only (personal) and one is used for programs (enterprise). Despite me using Typekit this is not a Typekit issue regardless of what Adobe support says, it is a login issue with the CC manager software although anybody with whom I chat (I cannot get someone on the phone) cannot see how that is the case and tries to pass off the issue to Typekit support.
I need access to both at all times. I was initially told by an Adobe chat rep that since the apps do not need a constant connection to the Internet to work (offline grace period) I could login to my enterprise, establish the license, log out, work as normal, and only need to log in to establish a license before the grace period ends. That I learned is not the case. Although it seems like a logical solution since if the program does not need to be connected to the Adobe servers it should not need to be logged in at all.
I thought for a brief period of time that I resolved the issue. Yesterday I was on on with both accounts for a while by logging in to my CC manager with my personal and into the application with my enterprise. but when I turned on my computer today I was logged into my CC manager with my enterprise account and all my fonts were missing when I logged back in correctly to my CC manager I was no longer logged into my programs.
This would be less of a hassle on a regular basis if it kicked me out of the Enterprise in the applications and I only had to log back into one account on a regular basis, not two.
I either need to connect my enterprise so that I can be logged in with my personal, install the CC manager twice, or make it so my applications do not need to be constantly connected online.
I also tried and failed changing my enterprise email to match my personal one, which needs to be the controlling account.
Please if anybody has found a solution to this problem let me know. Thanks in advance. 

Answer 1

Joshua,
I do see your point of wanting to have a separate account for your kits that you created.
You are not able to have two version of the Creative Cloud application manager installed on the computer.
When you sign out of your Educational subscription and sign in with your Typekit Adobe ID, it is a different profile as you know.
Switching back and forth could of caused corrupt data for the Creative Cloud app with signing out as it would remove fonts synced with Typekit.
Removing the OPM.DB file will help reset the CC app manager and you should see your fonts when you log in with your Educational CC subscription. 
You can still log in to the Adobe Typekit Webpage with your Gmail Adobe ID,  while being logged in to the CC app manager with your Educational subscription. That is thru a web session
When you sign out of the CC app manager for the Educational paid subscription, you deactivate the software session. You would be prompted to sign in to use the software when launched. That is why you are not able to use the software while being signed with your Gmail Adobe ID. It is not associated with the subscription. Can you try adding the fonts that you need from the Gmail ID to the EDU subscription? You should be able to add the kits and have the same fonts for both accounts. I know you mention that you want to keep the accounts separate, as I was thinking that would be less frustrating for you.
Thanks
Scott