Personally I think a lot of fans would love to be a matchmaker in theory. Making dudes fight each other seems like fun, even if in actuality trying to strike that perfect balance between entertaining match ups and relevant fights is probably quite difficult. Still, like fantasy foursomes featuring two buxom beauties and one snarky, less endowed Canadian actress, it's fun to pretend.
Middleweight isn't a very strong division in general, and this is especially true for Strikeforce's middleweight division. This seems to be the fight to make, and for good reason. Both are well rounded fighters and the fight itself will probably be entertaining. I'm pretty sure both Rockhold and Kennedy are both UFC caliber fighters, so this is a fight that is relevant to the division.
Rafael "Feijao" Cavalcante vs. Gegard Mousasi
It would be an exciting fights between to guys who can strike and definitely bring the violence. It also sets up the perfect challenger for King Mo for that vacant LHW title. Unfortunately either way we get a rematch, but it seems like the only real way to go at this point.
Tarec Saffiedine vs. Tyron Woodley II
A rematch sure, but if this fight is for the title and hence five rounds, we can see how these fighters can adapt in the championship rounds. Given how hard Woodley gasses, it might be an interesting dynamic. Saffiedine isn't necessarily a great finisher, but it might not totally suck if Saffiedine can somehow capitalize. The only other winning welterweight is Bobby Voelker, and unless they want to do Voelker vs. Saffiedine before the Woodley fight. It wouldn't surprise me considering this is Strikeforce, but it wouldn't make too much sense.
I just want to see Mein develop, as he is very young and has a ton of upside. Either fight works, and it will give Mein more cage time. Roger Bowling is coming off a win, but I don't think it matters too much either way. Tyler Stinson isn't too bad of a choice either.
I was thinking about pairing up Jacare with Jardine, but quite honestly I don't think Jardine is ever really going to compete at a high level again. The drop to middle weight doesn't solve Jardine's defensive issues. I think this is a fun fight to open up a card without too much consequence to the rest of the division.
I was going to suggest a guy like Yoel Romero or Roger Gracie, but on second thought I liked the idea of a Romero vs. Gracie fight instead. Larkin and OSP are guys that I'm not sure can make it in the UFC, so I think a fight between them is interesting. Both are guys who are probably going to be hungry going into this fight and want to erase the thoughts of their previous losses in this extremely "what have you done for me lately" sport. Plus they're both athletic and explosive. And black, so I doubt this fight can be faded.
I don't really know what you want to do with Lawler. He isn't great, but is probably better than a guy like Derek Brunson or any other prospects. I wouldn't be surprised if they had Lawler rematch Jacare, or just have him in case Kennedy gets hurt again, or have him fight a guy like Brunson and set him up for the next title shot if Rockhold beats Kennedy.