Hi, this is a very quick template setup. You need to setup template with Styles set- it is rather messy (

). You have 2013 so you can use Rich Text Content Controls as well. The estimator and estimator email CCs can be automated when you pick estimator the email auto fills. I don't have time now - but perhaps someone else does. I may have time tomorrow.
I have used Mapped Content Controls allowing data to be repeated.
NB: Don't mix formfields (legacy) and CCs - best practice.
Regards
Janine