Hi @RLandolt,
Yes, appointments in the calendars of your sales reps should show up as meetings on the contact record timeline in HubSpot. The requirement for that is not the local Office 365 or Outlook desktop add-in, but a connected calendar.
HubSpot notes that:
HubSpot automatically prevents any events from being added for members of your organization based on email domain (your portal’s target and connected domains), and existing users.
However, this seems to refer to meetings between users of your organisation only. A meeting invite sent from my organisation to someone else in my organisation and someone outside of my organisation showed up on the contact record of the person outside of my organisation.
The only person who needs to have their connected calendar set up for this is the sales rep.
Regarding your second question, unfortunately, I don’t know of any ways that would not include the call center rep in the meeting / activity – but this is more so a limitation of Outlook and less of HubSpot.
By the way, you might want to check out the meetings tool which helps with scheduling meetings and could solve the issue of call center reps being on the invite: Connect your calendar to HubSpot Each rep could create their meeting link (this cannot be done for them), the call center reps could then share this link with the prospects.
Hope this helps!