Re: captains license
I was skeptical of training courses, but a friend convinced me to give it shot. I must say I've really enjoyed the courses I've taken. I went through the Annapolis School of Seamanship.
It's not a bad idea to start documenting your sea time just in case you want to get a license some day. I did get my 100 ton license and learned a lot of useful information along the way, but don't dive into that as your first training course.