Hey Matt, we share a similar dream, and there are a couple of people here that actually making this dream come true as we speak. To start with, if you live in the US i recommend you finding an ASA (american sailing association) course - its a 3 day sailing course, and its the best course you can take for the $ ( to me it was $500 in 2016).

Also, follow @knot - this is a blog where all sailing content gets resteemed to...you can find a lot of experienced people there that can maybe answer your questions.

And welcome aboard steemit :)