Hi Joe,
I can only speak for myself, but I think everyone is going to agree a high impedance headphone is going to work best with a Crack. And the Speedball upgrade is no brainer.
I use Beyerdynamic DT 1990 Pro (250 ohm) exclusively with my Crack/SB. It is the perfect result for me. Excellent energetic sound. I am hoping to land a S3X soon but have some other priorities to deal with now.
I've used Sennheiser HD-6XX and they are exceptional also, and a fabulous deal. However, the Beyer's give me just a little more upper end clarity that I really like.
https://drop.com/buy/massdrop-sennheiser-hd6xx?mode=shop_openI have tried Grado RS-2e and they are much better on the Crack than I expected. I don't think they are badly handicapped at all. Nice to see Doc offering a great deal on the Crack/SB!