Am I headed in the right direction?
Yes, but you'll need to use format functions to properly compare dates. Example as follows.
[cb:parse function="time"][lastupdatedate][/cb:parse] Less Than or Equal To [cb:parse function="time" time="-2 MONTHS"][cb:date format="Y-m-d H:i:s" /][/cb:parse]
That for example would trigger if they haven't updated their profile in the last 2 months. The below for example would be 1 year.
[cb:parse function="time"][lastupdatedate][/cb:parse] Less Than or Equal To [cb:parse function="time" time="-1 YEAR"][cb:date format="Y-m-d H:i:s" /][/cb:parse]