@basdenhoed the short answer as I’ve known it is this:
Q1 - When sending a workflow email, it’s sent to the contact and does not aut-associate to the deal/company, no.
Q2 - Same as above. I’ve not seen a set up where sending an automated email will also associate it to the deal or company.
I could be wrong. I’ll tag a couple of friends to check with them. @Anton @karstenkoehler @Jnix284 @ChristinaKay @crispyGTM @KSenette4 have any of you all seen this done well?