Hi, Tall boys,
I'm late to the party, but just want to encourage you to give it a go, if that's where your heart and circumstances are leading you. I think, for a lot (not all) of boys in particular, elementary school is a pretty rough go, and some time home with mum might be just the ticket.
There are a lot of great free resources out there, if you want to give a few things a try to see what works the best for you and your kids. I think Melissa mentioned the Well-Trained Mind boards--there were several threads earlier this year that listed dozens of sources for free curricula. We love the free math from the University of Plymouth Centre for Innovative Mathematics Teaching, for instance. And the library is such a wonderful resource. We do buy a fair amount of curriculum, now that I more or less feel like I know what I'm doing, but there are lots of ways to get your feet wet without getting in too deep!
We've homeschooled from the get-go, so I can't address any transition issues from personal experience.
I know what you mean about being an obsessive planner--I've been reading university catalogues for at least two years now, and my eldest is 8! So I'm nuts, but there we go, that's not news. Whether or not the lads go to high school or not, I don't know (partly depends on when Frenchie decides to retire), but I figure it can't hurt at least to have some idea of which way we should be steering the ship, just in case we collectively decide to stay the course with homeschooling.
Well, when all the metaphors get too aqueous, I guess it's time to go...it has been pouring here for a month, and I have water on the brain, I think!
peace
minnie