This is a great idea and one that will be helpful to all of those thinking about cruising with their kids.
When my wife and I decided to cruise with our two sons and two dogs, we spent a lot of time planning every aspect of the trip - maybe a book would be better! When we first broached the topic of cruising with kids, years before we actually left, we talked about everything from where we planned to sail to medical issues and insurance. There was so much to think about that we split up the responsibilities so that we could get through it all. Here's my first stab at some of the things we considered. I will add to this over the next week.
Sailing with kids had a big impact on: the layout of the boat and where we were willing to sail - my risk tolerances when singlehanding are very different when sailing with kids.
Health and Medical insurance. My wife did all the research on issues related to health including: what to include with the medical bag - don't forget the dogs' issues; medical evacuation in case of a serious emergency; how to take care of wounds; good providers of health insurance; etc.
Kids love dogs and there was no way we were leaving ours home. We ended up getting "British Passports" for our dogs and were allowed into all islands in the Caribbean. This was a lengthy and expensive process but one that proved very helpful to us.
Transportation: the dinghy is the way around the harbor and we did not have the right one. I have thoughts on this and I am sure others do as well. Depending on the age of the kids, this may be a huge issue for debate.
Homeschooling concerns: what courses are best and how to get the most out of time with the kids in school. What impact does living on a boat vs. growing up in a traditional environment have - this is a big one for us.
Boredom - whether living on board or cruising for the week, kids need activity. One of the favorites of my kids was when I would read to them at night. I am no actor, but I did my best at different voices and they seemed to like it. We swam a lot and played constantly.
I will add more tomorrow - hope this is what you're looking for.