When can we expect trout to start hitting? Where are some good places and techniques to target them?

Speckled trout spots are very closely held by the anglers that fish them. I understand they prefer wet over dry areas, and prefer salt water over fresh.
Fall and spring can be the best times of year for trout. Other than that I can tell you that Rudee Inlet is a good spot, so is the entire Lynnhaven River basin. Casting around the rocks at the Hampton Roads bridge tunnel can be productive, so can the islands of the CBBT. In the winter, follow the crowds to the Hot Ditch. As far as baits, I can tell you that most people use them, of one type or another. Mirror lures always worked well for me in the shallows, but I've never really targeted trout much, so this is the sum total of my knowledge. Hope it helps.