My DD wont be going to school unless we agree it together later on. She's younger than your son so HE isn't official till the September of 2010 but don't see it as being any real change from having her home up till then anyway.
I think home ed is the better option, so I'm not planning HE as a reaction to schools. There are even some good schools (read good as similar to the ethos I'd pick rather than OFSTED good) in the area, and some that have made flexi-school arrangements with families already. Its nice to know they're there if I need to change my plans at some point but doesn't change my mind on DD carrying on at home. I don't mind later if we make a decision together that DD is going to try school, but I wont be pushing the idea.
I'm not with DD's dad, and he wasn't convinced about HE at first. Without going into the whole story I'll probably sound like an awful ex, but basically by the time we got through the other arguments to the HE argument I wasn't prepared to discuss it with him at all unless he went and did some serious research first. I figured that while I was going against what's 'normal' - it was him that wanted to make a change to what was already happening. DD is doing fine at home so why alter it. I think that if DD had gone to school, been generally ok but then I decided HE would be better I'd feel more like I had to find some evidence/information about it before I made another change - but I'm pretty sure I could find enough to convince myself it was the right thing to do.
It seems to be a pretty common theme that the parent who is with the child most of the time is keen to HE and the other parent isn't so sure (and I've heard it both ways round too). It doesn't seem to be limited to separated parents either. I wonder if its like the idea that new mums are having 'time off' when actually they're with a newborn almost 24/7. So unless you've been there and experienced it or you have a very open mind about it then its hard to understand the ins and outs and whys of it.
I don't have a period of DD being in school to compare the effects with, but so far things are going okay. I've had to make some compromises because of being single but so far nothing fundamental. HE is one of the things that is really important to me and that I would compromise other things for.
I'm finding that some friends we've seen with children DD's age are drifting off as their children go into school or nursery. But the ones' we've become real friends with as opposed to play/coffee dates are making the effort to keep in touch and us with them. In fact DD being home means quite often we're the first call made when they have a random day off because we haven't got another nursery/school timetable to stick to. There aren't lots, but I've always thought that with friends the quality is more important than the quantity and don't see why it would apply any less to children. Not long ago DD started making real friends and although I like their parents its not the same as being whole family friends so I have to try harder.
To make sure we don't end up lonely we've been mixing with HE families online for ages, and more recently a local group got going a little. Ex has gotten more involved here too. We do find that we're the odd ones out a bit because of being separate but so far it hasn't been a problem. There's enough of a mix of personalities and lifestyles that it isn't a blinding difference. I think its harder for him, but I think that's because he's a dad and its mostly mums there day to day, rather than because he's single.
I think that in some ways it'll be easier for me to HE separately, with my ex and me each taking charge of our own time with DD, than it would have been if we were ever a couple and I was home with DD (+?) and he was coming home expecting to see progress etc. But that's pretty specific to us, not other couples/parents or other styles of HE.
I've never had the traditional family set up for myself and DD, so I don't really miss it. Sometimes I do get bit wistful about the idea of it. But generally I'm happy as I am.
I don't think it would be as easy (lol, maybe easy isn't the right word) without the support I have from my family - but that isn't a HE issue so much as a lone parenting issue. It might be more difficult for a lone parent if the HE caused problems with family than it would be for a couple who can rely on each other for support. That isn't a problem for me but it might be something to find out about first.
I live at my mum's, through choice now as after 3 years I'm actually near the top of our social housing list and when I bid on a house I've actually had an offer, so I quickly stopped bidding. Its more like living with housemates than Living At Home, as there are other adults in the house too.
Support/company wise it helps to share a house and for me it does financially too, although on benefits rent doesn't count if its family so I've never got anything towards things like that - but the cost of living is so much lower sharing things (utilities, phone/net, meals, etc). But it is hard sometimes too. Its not a deal breaker either - I'd still HE if I moved out. I'm pretty sure I'd manage to.
Something I do wonder is if I'll ever find enough space of my own to move on and meet someone else. (As awful as it sounds to say it, if I had more than one child I don't think I'd even be considering this as an issue. But I don't feel like my family is complete and I am still young) But while the HE, and so having a slightly weird approach to life, childcare, staying home, etc seems to make this a slightly bigger problem again I think its a lone parent thing not a HE thing. After all if DD went to school and I worked while she was there - I still wouldn't have any more time to my self really.
You don't mention working, but I'll share anyway seeing I'm rambling on so well. Knowing I wanted to do this for the long haul I thought about it in advance and decided I could work and HE. I'm self employed. At the moment, with a very young DD, I'm doing as little as possible out of the home - with lots of hours working on things I can do at home to prepare for later on when I work more. I think that compared to the general population quite a lot of single home educating parents are self-employed because it can offer so much flexibility and they can combine it with HE. I'd be happy to talk more about it if you wanted more info. At the moment I don't use childcare outside of family - try to fit everything I can into times they available or when DD with her dad. I do know of other lone parent who are employed and HE so that is possible too if you can arrange things right.
I don't know if any of that helps at all but it was nice to write it out and think it all through, sometimes I feel a bit like I'm just falling into it. But now I know that actually I'm not at all - I've planned and arranged things in my mind that I didn't even realise I had.