Working your Way around the world with kids

I've been reading quite a bit on here and although I might be wrong, it seems that most families that are doing long term travel here either have saved for years and have ALOT of money set aside for the trip as well as job to go back home to OR have some type of ability to continue earning money while on the road...tell me if I missed something! Anyway, so my question is what do you folks that are experienced in taking off for a great adventure think about saving a little money ($30,000) and selling everything to travel for an indefinite amount of time?
We have 2 school children 8 and 10 that we would have to 'road school' and plan to start out by going to Greece where we have Greek relatives to visit and then move onto countries like maybe Turkey using places like Wwoofing and workaway to help keep down expenses and really get to know the culture. We would eventually end up in SEA and I already have a BS and plan to get certified in TEFL and settle in to work for a bit and then figure the next out from there. Problem is, we won't really have anything to come 'home' to in the US other than starting over so the cycle might just continue as our new mobile lifestyle!
This is very very preliminary so any thoughts, critiques, ideas, websites and opinions would gladly be welcomed! We want so badly to take the leap but do not want to fall flat!!!

Let's define "ALOT"!!!!! After travelling for fifteen months we had spent about double your savings - but there were ten of us, so for four people the money you already have could last much much much longer. With that thought in mind I would tend to hold on to your house if you can so that you do have something to go back to if you want. A roof over your head is not to be sneezed at. You can always sell it if you discover you don't want/need it anymore. OTOH it might provide a stream of income for you while you travel (tenants' rent from our place paid for insurance and rates etc while we were away) Or could you downsize to something that would be a suitable retirement-type home? This would at least give you a base to fall flat on!

My husband had a rewarding job to return to - if he had not, we would have been excited at the prospect of spending time elsewhere teaching and living. In fact the very day he went back to work there was a job offer in his inbox for a two year position in Istanbul where we had just returned from. It was tempting, but he had just accepted a new position at home and wanted to proceed with that. We had originally planned to only travel for a year, but once we were enjoying life on the road hubby applied for an extension to his Leave Without Pay and was granted an extra three months with the condition that he then return! The thought of moving indefinitely would be very attractive to me. Even with kids. I'd encourage you to go for it.