Ehm - why are you using a public question instead of a direct message if you want to ask me specifically?
Also, I am not sure where you need specific support. Do you have any problems implementing that requirement, or are you looking to understand some technical concept better so you can implement it?
Your requirement sounds straight-forward. If you map users and managers in a datalist, you simply need to have a task listener lookup the relation and assign the escalation task accordingly. Same with the DB based lookup, only that you'd need to include a custom SQL call to a separate DB.