2. There is, what appears to be, a small amount of outboard oil dripping from my engine when I pull it out of the water. I don't see signs of the leak above the lower unit.
Get a seal kit for your lower unit. You will need 1/4-20 threaded rod and a harmonic balancer puller to get the bearing carrier out to reseal. If you have a manual it will help you do this in no time.
Your only problem will be removing the retaining ring that holds the bearing carrier in. Thats why you need the manual. It will have step-by-step instructions and make your life sooooo much easier.