Dusty Dog Ranch, small world. Yes, I have spoken to Behan by email and have the book Voyaging with Kids that she co-authored. She is a wealth of information. I really admire their accomplishments. Not many long-term cruisers make 8+ years with 3 kids. Well, that's not true. Just few have the time to write about it.
I know that Andy from 59 degrees north Podcast is a fan of Mr Money Mustache and there are a few others like Sailing Simplicity etc. who talk about budgeting.
I think most of the 'Go Simple, Go Small, Go Now' types who do this take a sabbatical or throw caution to the wind and plan to work later in life to make up the lost income. I feel we are different. Our plan is to save hard now and use income from our investments to pay our way. We want to cast off when we are about 40 with kids who will be 5 and 7 by then. Problem might be finding a bluewater boat that doesn't eat the nest egg.
In an ideal world we would start in the Bahamas/Caribbean for a season or two to feel out the life and boat and then make our way through Panama, and do the Puddle Jump. Australia might be the end point, but we dream of doing a full circumnavigation very slowly like Totem.
Muckety_muck it sounds like you have similar aspirations. We have been lucky to have the opportunity to travel a lot (50 countries), even with our kids, and I have to say the world is more hospitable, safe, and easier to navigate than most people think. That said, I would definitely look to be spending months if not years in places. The idea of rushing this to get back to a job, or because we were running low on a sailing kitty is exactly what we hope to avoid. I think it is safer and more fun that way.
Oh, check out Erik Hemingway and his Family Adventure Podcast for some other like-minded cruising families.
Fair winds