sell up and sail

A more serious post, and less humdrum sailing news... We're getting steadily more serious about the idea of 'selling up and sailing'.... We reckon that if we realise all our assets, budget £50k for a boat, then we can survive on £600 per month for about 15 years before we'd need to seriously consider working again on anything other than an ad-hoc basis.... Scary proposition though, as it means having nothing when (if) we return.... except a boat, and hopefully a pile of memories... Off the top of my head, big concerns for us include:

1] Schooling for the kids.... could we be dedicated enough to school them for 3 hrs a day, 5 days a week, and even if we could, would it make the 'dream' less appealing?
2] Family health back home - I guess this is a standard concern
3] Finances... what if something major broke, and we couldn't afford to fix it... engine/new sails/rigging... I guess this would just cut short the timeframe
4] Ability to find work after our return - maybe a mute point... I suspect that if we do this, we'll be unlikely to return!... but even so.... my current skills in the IT industry will be next to useless after 15 yrs!
5] Kids, and their integration into 'the system'.... assuming they decide to go to Uni, will they ever fit in?... will they find the structured environment restrictive?..... will they have the neccessary group social skills?... if they don't take the higher ed route... when/how will they enter the world of work?

Ironically, the bit that I suspect troubles most people, the reaction of their families isn't a problem... we've very briefly floated the idea past both sets of parents, and they both think we'd be mad not to do it!... sisters are a different matter... both firm participants in the capitalist system, and busy climbing the personal wealth ladder... can guess what their response would be! I was also personally concerned that this was my dream, and that I would be dragging SWMBO along as an only partially eager participant.... but she seems to be getting keener and keener on the idea, and is now talking about it more and more..... I guess neither of us have jobs that have us flying out of bed in the morning, eager to face the days working challenges, and both dream of a better life with other concerns than paying the mortgage, running the car and paying the electricity bill..... Ho hum.... contemplation required methinks...