Can't help but feel the show has set them as two sides of the same coin showing transactional marriages and if/how the "love" aspect of that equation can still exist.

Connor and Willa are absolutely transactional and seemingly one-sided with Connor showing more interest romantically . This uncertainty about their future bubbles over time but on their wedding night they finally get to the heart of the issue and are completely truthful with each other. There might be some cracks upon close inspection, but you know what, it is authentic. They aren't playing each other and are being straight up about the situation. The money is the main attractor, but it doesn't mean they can't carve out a little world for themselves that isn't unified, loving and supportive.

Shiv and Tom are transactional as well and seemingly one-sided as well with Tom more interested romantically. However, I think Shiv does love Tom deep down, but she doesn't want to admit it. She feels safer compartmentalizing the marriage as transactional and never really breaking through to the vulnerable, loving half of it. So on the night of their wedding, they have a different kind of conversation. Instead of meeting halfway in the middle like Willa, she threw a nuke down and called for an open marriage.

Shiv and Tom's wedding is sealed by a fateful death - one of a lowly waiter. The boy is a nobody, so the real story is buried with ease and the world marches on. Years later and the truth is still protected. Almost like a symbol of "the game" itself -- true power, class, and the corrosive elite lifestyle our characters maneuver through constantly.

Connor and Willa's wedding is sealed by another fateful death - the inverse of the lowly waiter -- Logan Roy himself, the titan looming over the entire series. Despite their efforts to contain the news initially, the kids don't have the luxury of dealing with the death of a nobody this time. It doesn't take long for word of his death to leak, and there are immediate financial ramifications to the stock price.

In short, marriage is always a transaction in some way. It's almost like Tom/Shiv's wedding day was a literal representation of marriage tipping towards a business move, highlighted by a death which neglects the humanity of it all.

Connor/Willa's wedding day represents a transactional marriage maybe tipping towards a loving union, highlighted by the death of, well, the literal embodiment of the transactional, cold-hearted approach to relationship in this universe, Logan Roy.

Connor seems freed in a way from his father's death, marrying his bride to an empty crowd despite his absence. Tom on the other hand, is anything but free from Logan's death. In fact, the opposite. It is like he paid a debt with his heart the night of his wedding, and that debt is finally coming due with Logan's demise. He hitched his cart to the wrong horse, made his bed, and now he is going to have to lay in it.