fonts - serious errors - Catalina

REALLY frustrated at the moment and posting to see if anyone else has similar issues... Just bought a shiny new iMac (with Catalina obviously). I'm transitioning from and older computer (El Capitan) where I have old fonts - but they still work for my buddy who is using High Sierra. But when I try to load them, I am getting "font errors" that basically is the red flag warning with the instruction of "do not load them".

I'm just sort of at a loss on how to proceed. Repurchasing newer fonts would cost a fortune ($400 for Helvetica!) The fonts I'm using are old, but they were paid for... and again, they work fine on High Sierra.

This doesn't seem to be an issue with being corrupt either, I've tried multiple saved copies (backups, etc).

This seems to be just Catalina.

I'm also seeing that like in a "suitcase" of perhaps 8 fonts, 6 of them are ok, but two are not. I can't seem to find any way to "extract" those 6 good ones.

(side note of frustration: I searched here on the apple help for various help like "font errors" and all the results are coming up from like 2013, and I can't seem to filter the results to only Catalina, of even results from the last year.)

Frustrated and not sure I have any other option but to ignore the warnings and install the fonts and just hope for the best. What a way to start off with a brand new computer.

(sorry for the griping, I'm clearly upset at all of this).