TUNE
Ditch that hypercrap tuner. Get a tuner from BlackBear performance. Here's a link for more information, or post in their sub-forum. Get all of your mod's done first before you tune.
http://www.blackbearperformance.com/
Gears/Traction
With 285's, I have factory 4.10 gears with the G80 in my Silvy (different vehicle, I know) and I have great power compared to one with 3.73's. So anywhere from 4.10's to 4.56's would be good for 285's. Even 4.88's but that seems like too much gear for that tire size.
To keep that power on the ground and keep traction, get rid of your G80 (if equipped) and get a Trutrac or similar traction aid for the rear end (can not install a locker in the factory IFS differential fyi)
Transmission
Depending on your transmission miles, I'd recommend a higher stall on your converter, shift kit, and a corvette servo. If you are rebuilding it at some point, go with my recommended upgrades along with better clutch packs and a "beast" sunshell
Engine
Along with your current upgrades, I'd look into headers (long tubes if possible), high flow cat's, ignition upgrades (plugs, coil, wires) and injector upgrades. Electric fans also for cooling, and a lower temp t-stat.
If you plan to go further into the motor, then start reading up on cam's and other internal parts. I had a homemade intake, coil, plug wires, exhaust and a built 60e with 3.73 gears and 285's on my 1995 (TBI however) 2 door. Power as okay for what it was. The 5.7's really don't make that great of power though compared to a LS motor. If I owned a OBS still, I'd be swapping to a LS based motor.