My Woods BB60 Brush hog is 3 years old. I generally check the gear oil at the beginning of each mowing season, and maybe once during the season. During the mowing season, it's on the tractor frequently, and gets parked in a garage with a cement floor... this lets me quickly see (by any spots or puddles on the floor) if any of the seals are leaking. If not for that, I might check more frequently.
The area I mow is pretty rough. I hit a lot of stumps and rocks. If it was just grass/meadow without all the obstructions, I wouldn't check even as often as I do. (I'd rely mainly on the "puddle on the floor technique" to tell me when I was losing some)
John Mc