For steaks, in a 12-inch skillet heat oil over medium-high heat. Reduce heat to medium. In a shallow dish combine flour, paprika, salt, and pepper. Dredge steaks in flour mixture (reserve any remaining flour mixture). Cook steaks, uncovered, in hot oil for 4 to 5 minutes per side or until medium (160 degrees F); top with cheese the last 2 minutes of cooking. Set aside; keep warm.
While steaks are cooking, place tomatoes in a food processor. Cover and pulse with several on-off turns until tomatoes are coarsely chopped.
For Tomato Gravy, in the same skillet cook and stir garlic in oil over medium heat for 1 minute or until garlic is golden. Stir in tomatoes, snipped sage, reserved flour mixture, salt, and pepper. Bring mixture to boiling; reduce heat and simmer, uncovered, about 5 minutes or until desired consistency. To serve, place a small handful of arugula leaves on each plate, top with a steak, and ladle on some of the Tomato Gravy; pass remaining gravy.