Adding more material to the stop is a guessing game. When I've done it, I've often had to grind down quite a bit. And it depends how much has worn away. Also, I've heard that it's the frame and not that stand that wears, but I had always added metal to the stand.
I left the welds on my 84 R100 a bit too proud and it barely wanted to stay on the stand. At first I even ran a strap to the stand to prevent it retracting on its own - not taking any chances! But I knew after using a while it would pound down a bit, which it has done and is about right now.
I'm pretty careful when using the center stand - putting it up gently (slowly) so it doesn't pound against the stops. That can be a little difficult, since it's easier to get it rolling quickly to have some inertia to carry it up onto it.
Also, I'd caution against riding the bike off the stand! The screws (or bolts) retaining the stand can come loose and the mounts in the frame become damaged. It's not a simple task to repair. The extra weight of a rider when deploying the stand can be enough to work them loose, or grind into them making them sloppy. Go as gently as you can on these things!
And you DO want the wheels off the ground when on the stand! That's necessary to removing a wheel.
One other thing - I've had my larger bikes try to get away from me when getting them off the stand, so any more I leave the bike in gear when parked. That way when it comes down off the stand, it can't possibly roll away. It stops right now! Usually it's a problem on uneven surfaces and the bike wants to fall away from me. Since doing this I no longer have close calls.