Changing oil in foot of boat motor

[wiperhunter2]

I had not changed the oil in my foot for a couple of years and since my prop hit something earlier in the year, I thought now would be a good time to change it and make sure no water got in there. I drain ed yesterday and let it set overnight to make sure it was well drained. No milky color in the oil, so all is good I hope but I have been noticing some slight leakage come from what looks like a weep hole. Has anyone ever noticed small amounts of gear lube coming from their motors foot before? One other question, how do you fill your foot on your boat motor? In the past I have just trimmed my motor up and put the oil in from the lower hole, until it started coming out the upper hole but it occurred to me that I might not be able to fill it up completely, unless the motor is vertical.