Welcome aboard nightrider.
Capt, here's a little bit more info about myself (as well as a partial answer to rockDAWG's advice).
I do plan to get my ASA 101, 102, 103, and 105 before going on this trip - or any that involve getting out of sight of the launch on the lake I intend to frequent.
I have absolutely zero experience sailing, but am a fairly experienced (and trained) powerboat operator, as I operate a small rescue boat as part of my job. I would imagine that sailing and operating a powerboat are apples and oranges; just thought I'd throw that in there to say that I'm comfortable on (and respectful of) water.
As far as intended vessel...that's a bit more open right now than I can intelligently discuss. It's really going to be a matter of what I can find that meets my needs - which I am still zeroing in on. I had already planned, when I have a specific list of what I'm looking for in a sailboat, to post that here. Love this forum.
Again though - not putting anyone on the spot for specific answers. Just generally speaking, would say, a MacGregor 25, or a Catalina 22, or a SJ21...y'know, just a decent trailer sailer...be able to make this trip safely, assuming that the crew was physically fit, mentally prepared, and well trained before hand?