The answer to both questions is don't worry so much.
Your rear tire is going to square. It's the nature of the 500. This amount of squaring at this point in the tire's life probably indicates the previous rider didn't keep the pressure up to specs. Run the life out of that tire. It'll be just fine. When you're ready for a new set, consider the Battlax BT-023. It has a more linear tip in and requires more deliberate input. That should give you more confidence leaning over. I personally prefer the sharp tip in of the stock Dunlop, but the Bridgestone is a better tire overall.
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Male, 44yrs, 180lbs, 5'9", '14 (RWB), 22k miles, Bridgestone BT023, Vortex V3 kit, Rotella T6, KN-204 filter, 87 Octane, Maxima Chain Wax, Puig 6479W windscreen, clear signal lenses, Fork Preload caps, T-Rex spools, Radiator guard, Shorty adjustable levers, Fork stem RAM mount/USB port, red/black alum grips, 300R Rear tire hugger, Rear seat cowl, LED engine/undertail lights w/RF remote, LED position light, Sea level, city commuter, spirited rider, turn my own wrenches.