Lessons and licensing would be a very good beginning point, thanks for reminding me about that. :P I've done a tidbit of research into it but not a whole lot. I live in Kentucky so opportunities there are a little lacking, but I'm sure someone around here does it.
I do realize that building a boat is more than quite a bit of work, but I figured if it was done in spare time over a good amount of time (5-10 years at the most, perhaps?) then it wouldn't be too taxing on me, and I could hopefully save up more funds in the meantime for any journeys taken. With that said though, I do think I lean more towards just buying one. It's easier and faster, but like I said before I want to start small and see how difficult it is for me. It would be nice to be able to point at something and say "I built that." It would be even greater to point and say "I built that AND I sailed it around the world"! Haha!
I think before I do any crazy circumnavigation though, I'd like to do that "great American loop" around the Eastern US. To clarify! I don't intended on just up and buying a boat after I get all the proper training / qualifications out of the way and sailing some ridiculous distance. I'd practice on some lakes around here. Stay in the boat for a few days, maybe a couple weeks just to see if I'm not biting off more than I can chew.
Thank you all for your responses! They're much appreciated!