If you don't like working on boats I would look at something else. Your kids may would rather use the boat right away than watch you work on it .
This statement may have been overlooked by many here, I don't know, but I think it's a very, very important one.
There are any number of reasons to acquire a cruising boat. Some people really like working on them. Repairing decks, refinishing wood, reupholstering interiors, painting, etc. are what they really like to do.
Some people like the challenge of preparing a boat for a specific goal--- a long voyage like the Great Loop, the entire west coast, trans-ocean, etc.
And some people simply want to start boating the moment they acquire a boat.
While it sounds like Greg's decision may have been made for him by the engine survey, I think the validity of Pack Mule's statement rings true for whatever boat he ends up contemplating.
In 1998 when we decided to buy a boat rather than continue chartering the broker we used found us a prospect in California. Alameda to be exact. We, with the broker, flew down to check out this 1973 boat and have its hull/systems and engines surveyed.
Because we knew nothing about cruising boats like this outside of our minimal charter experience, we paid the expenses for a good friend who's entire career has been with one of the more prestigious marine propulsion and generator manufacturers in the industry. He knows boats like this backwards and forwards and didn't care if we bought this particular boat or not. We wanted an objective set of eyes with us and there weren't any more qualified than his.
After the inspection, sea trial and surveys we had to make up our mind to buy the boat or not. Our friend delivered the statement that made our decision. I'm paraphrasing but he said, "This boat needs a lot of work, much of it cosmetic. But what's important is it's a boat that you can begin to use and enjoy as soon as you get it home. All the issues that need addressing can be taken on as you go. But you can start using the boat right away. You aren't buying something that you have to spend a ton of time and possibly money on before you can even start using it."
Given Greg's stated reasons for wanting a boat of this type it sounds like our friend's comment is equally applicable to his situation. With the desire to start cruising in a boat his family will enjoy while his kids are at an age to do so, it would seem that being immediately usable should be a top priority in determining if a boat is suitable or not.