A bearing for a 25.00mm shaft will start life with an ID of 25.12 to 25.22mm, so 1-2.00mm we would consider worn. This is for composite cutless bearings, rubber may be different.
I'm not sure that this is an 'exact science'. For instance how long is the distance between your gearbox and the cutlass bearing?
If the proshaft length is considerable, then a small amount of play at the cutlass bearing is not going to make a tosh of difference, especially if there is some system of flexible coupling prior to the gearbox.
Sorry to be so inconclusive, but details are all important to be able to be more precise.