I'm considering an award ticket - Florida / ATL / PIT.

I'll likely try to book it with as close to the 4 hour layover limit as possible, but, I'd like to make it a little longer to go into the city to do a couple of things.

So, I know it would technically be gaming the system - (thank you for NOT lecturing me), but, I'd like suggestions as to whether or not I should book an early flight leaving Florida, fly the first segment, then try SDC or SDS for a later flight to PIT once I arrive at ATL - - OR - - should I book the latest flight to PIT and try SDS / SDC for the first flight.

I think if I do SDC for the EARLIER flight, the phone agents would likely only rebook me all the way thru to PIT, which wouldn't give me any longer than a 4 hour layover. I could just try to SDS at the Florida airport, but would they let me take an earlier flight to ATL without rebooking me all the way to PIT?

Or . . . is this simply is unlikely to happen at all!?

Also, I'll likely have to check a bag after some shopping in Atlanta. How do they manage checked bags if I can only do stand-by?

Any thoughts?