As far as condition, clean is good. Water or milky color is bad. The bottom plug is magnetic. If it has chips stuck to it, you are having some wear on either the shift dogs, gears or bearings, but it is probably shift dog wear from slow shifting or shifting with the engine above idle. A very fine grey smear is OK, just wear on some part. The quantity for a BF 90 is slightly more than a quart. The BF 40-50 may be less. When changing, make sure the vent is open too, otherwise the oil will not drain, and you cannot get much to go in either. I am sure they are at least 16 ounces or so. There will either be one or two vents higher up than the drain, and the magnetic plug is in the drain. I also change the o-ring or gasket each time the vent and drain.
I change it twice a year, since I don't ever want to find out I ran all summer with salt water in the gear lube. I lost the gearbox on a Johnson 2 hp from neglecting the lube changes.