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Rethink this, rethink this, rethink this. 68 foot is way too big for a newbie. You absolutely want a captain for the first several years. You can still "drive", but you'll need him when the s--- hits the fan weatherwise, windwise, seawise and mechanically, etc. etc. WHICH IT WILL eventually. It could make the difference between solvency and bankruptcy AND living or not. Your relationship with a captain will be more like friends, so look at personalities as well as experience. Look for a 100GT captain on at least his 2nd issue (over 5 years experience) Less than 100GT lacks experience; over that and he probably works commercial boats which may make him a little rough around the edges.
In today's market you could pick up a 4 or so year old boat with less than 500 hours for 1/3 to 1/2 the price of new and that's just broken in. Be sure to have it surveyed of course, and plan on swapping out the electronics for more UTD stuff, but don't go crazy for the latest/ greatest that will just mezmerize you and leave you playing video games instead of being able to actually use it.
Your captain doesn't have to be full-time if you can't afford. I manage a few
boats (Not a solicit- I'm not available) which means I get a monthly base fee then charge by the day. We schedule the season in advance which gives the owners incentive to use the boat more than they normally would. It's a good idea to line up the captain before buying the boat to have him help you seatrial. He'll be looking for things that the surveyor won't such as fit & finish, seakeeping abilities, and other things geared toward your comfort.
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