Booking Direct vs Booking With a Group

We just got back from our 7th trip in the last 2 years and had another great time! My other half has a great travel agency through her job and each of our past trips was booked through them. They no longer book to Hedo though so this time we booked direct. What we didn't realize though is when you book direct, you don't get the Club Hedo rewards unless you stay a minimum of 6-nights (we stay 5 nights each time). This got us talking about booking with a group. What are the pro's vs. con's for booking direct or with a group?

What we have noticed is for us it’s cheaper to book direct or through TA because you’re getting a package deal. When going with group you are only getting hotel at discount and then for us it’s another 1500-1600.00 each for airfare. So we usually book direct.