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Tyler,
First understand that most yacht captains don't see home or family much. Second, except for on the big boats you won't get rich. Third, it's all rep and that takes years of dues paying to acquire. Fourth, you have to make your own breaks.
As for myself, I grew up boating but entered this business in my late 30's. I got my ticket and worked in an old boat yard to learn maintenance and repairs from the pros. Then got a gig cleaning oil spills, did some p/t deckhand and relief captaining on dinner boats, a few transports and anything else I could grab. When slow season came I started my own small tourboat business and ran that for 5 years. Later on I managed 2 marinas and transported while I gained a local rep and now work for myself as an independent. In other words, don't look for security in this world and be real flexible. The only reason to be in this business is for the adventure.
You need to work your way up to 100GT to be taken seriously, but if you want to work the small boats (under 90') you probably don't want to go over that because you'll be considered too rough for the family cruiser types.
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