“Is there some way to have SQLyog sort of ‘automatically’ decrypt and encrypt data?”
Short answer is NO. SQLyog will display what is stored in the database (unles you SELECT AES_DECRYPT(..) etc., of course). And there is further one more problem. An encryption algorithm may result in a string containing the NULL-byte (X00) and such data would be identified as binary data. And you should use binary datatypes (VARBINARY not VARCHAR and not at all numerical types) for storage if you really want to do this.
We have discussed many years ago to implement such feature, but decided that it would not be a solid business case for us.