What is the output of 

ssh -vvv g...@my_personal_account.github.com 

and 

ssh -vvv g...@my_work_account.github.com
?

There might be a clue in there to the reasons behind the troubles.
I've been using git with multiple identity files and a single server, 
differentiated only by hostname with no problems.

HTH,
Alan

--
Alan Hawrylyshen
a l a n a t p o l y p h a s e d o t c a



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