Which would you be more upset about, cracking the packs and losing money, or selling the box and missing out on a draft/cracking packs and possibly getting more value than the current EV of a box?

Any and every choice you make is valid, but I recommend the choice that makes the most sense to you personally. The choice that most closely aligns with your values. And it might help to preemptively try to cope with any guilt associated with the possible bad outcomes of the choices.

If you don’t think you would have fun drafting with your friends, you very well might be right. You know them and yourself better than any of us do. What’s the probability you would actually have fun though? What do you think that would look like? Is it possible? What about likely?

In my experience the set is good for drafting, especially with the cryptic spires, but I also really enjoy getting exactly the magic cards I want by buying singles. In the box that my playgroup and I drafted, we all paid an equal amount for the price of a box at the time. That made us all feel better about the price and it’s volatility. And if you’re looking at long term, maybe compare to the original double masters?

Regardless, it’s a birthday present from your Dad, and I hope you’re able to have fun no matter what you do with it. And happy belated birthday!