I think your plan to fill and test is a good one. That is what I would do, except for the analysis. There is always a tiny fuzz of steel on the magnet, so analyzing the oil probably won't be able to distinguish between normal wear and serious damage. Debris on the magnet are your best tell.
Signs of damage are:
-Noise; whining, howling, grinding.
-debris on drain plug chip detector magnet.
-Serious wear can show as clunking between drive/overrun (hard to distinguish from gearbox dog clearance).
-Gear teeth turning blue (pinion gear always goes first).