All very helpful comments. Each reply has been quite helpful and what I was looking for, so thank you.
The $1500 boat's ad, in addition to the survey that the seller provides, says: Comes with new handrails and racing rudder., portapoti, alcohol stove, full compliment of sails., cradle, and 8 hp Yamaha motor.
The $2400 boat's ad says: Includes many extras: Jabsco Marine Toilet, Hood Furling Jib, Force 10 Marine BBQ, Johnson 8.0 HP motor, 2 mustang inflatable PFD, 5 floating cushions, 5 adult Keep Afloat Lifejackets, 1 youth Buoy O Boy jacket, sleeps 4-6, winter tarp, folding cradle, must see.
I spoke with the $2400 owner last night for a bit: he's an older gentleman who's looking to sell because his wife passed away and she was his sailing partner. That said, he didn't provide a lot more clarity for me than what was in his ad - he's a bit of a rambling man. His boat is being hauled out tomorrow morning.
So, my wife and I popped by the club to have a look at the boat while it was in the water -- the owner couldn't match our schedule, which may or may not be surprising given I let him know this morning. I felt it was a good idea for Sharon to see the boat and get her reactions/thoughts. She was happy with the size of the boat (didn't feel it was too intimidating in size) and was pleased with the size of the cockpit. She's thinking of us having another couple, some of whom have small children, come out on the boat for a day trip and thinking of the boys having their friends on the boat as well. Since the boat's coming out tomorrow, sails are off as well any of the accessories and we obviously couldn't get a look in the cabin.
I like the idea of having a boat for when Sharon and I finish our sailing course in May and can go out and learn the ropes together. She's really not sure she likes the idea of sleeping in this boat, given it's size and it's movement, and that's really useful feedback. She's totally cool with daytrip and such, but not sure an overnight experience is for her. In a sense, that seems to confirm this size of boat as a first foray into sailing...we'll do this the baby steps way and in a way that suits everyone.
So, I'm going to go back to both these gentlemen with essentially the same list of questions. I'm looking at this as a bit of a learning experience -- the whole process is obviously brand new. One of the interesting things I learned was that both of these gentlemen belong to the same sailing club, but the $1500 boat hasn't been in the water for a couple of years and the owner hasn't really been doing much work on the boat in the interim. Coincidentally, his survey was from 2 years ago, prior to the boat being put into the water.
One thing that stands out for me right now is that I've no clear sense of gear and equipment that's included with the sale of either boat. In some ways, the $2400 boat is attractive given the extras that it has (including sail covers), which I would likely buy for the $1500 vessel and the costs of which seem, at the moment, to outstrip the difference in pricing. That said, a solid marine survey that's two years old is better than no survey (maybe?).
So, hopefully meet with the gentleman during haul out tomorrow, and then ask both sellers if they have lists of what gear is included in the sale. I need to do some other homework regarding payment of fees and such, as well as insurance, to have a decent picture of where I'm at.
And yes, while it's true I'd like a boat for next year, it doesn't have to be either of these boats. What's clear is that we can learn from these experiences, and if we do have a boat at the end of going back and forth with these men, then that'd be a bonus. We're not over a barrel and as correctly pointed out, there's other boats. But I don't want to procrastinate, either.
At some point, we're going to have to dive in, and I know that I at least have spent more money on worse things.
Thanks again. I'm struck by how this forum seems to have limitless patience for the noobs who come on here...