will the sugar steak with bourbon go well with arugula and parmesan salad?

I think so too. I often serve thinly sliced, rare grilled steak - flank, flat iron, hanger, etc. - with various marinades, over greens dressed in a simple vinaigrette. The bite of arugula is an especially good balance to steak's richness. Definitely add a few parmesan shavings - sweet from the marinade, salty from the parm.... I want this dinner right now!

Yes, I think it would be delicious.