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Daft question - do you succession sow the overwintering veggies like cabbage, kale PSB etc?

Umm...... d'know either.... I would think yes for cabbage, no for psb.... as cabbage is 'ready' at a specific time frame, where as psb sprouts for a month or so IME... maybe

No, I don't.
Can't really see any reason why you would, as they generally need a long growing season and would probably not become a big enough plant if sown later.
I did (accidentally) grow 2 lots of spring cabbage this last winter, and they all matured about the same time except the later ones were significantly smaller.

Edited to say (after putting brain in gear) ...
Overwintering veg like cabbage, sprouts & PSB mature as a response to winter temperature and day length ... not the length of time they have been planted. So you would get the same effect as my spring cabbage, maturing at the same time but smaller.

I've never heard of anyone planting brassicas - the slow growing ones. It's only quick growing veg - peas, radishes, turnips (small white ) etc that usually get grown this way - I presume it's because they're not only quick growing but also quick to go over.

I've done successional sowing of my swedes (large, orange :-)) though only two batches, two months apart. Funnily enough, though, I am bringing on some early PSB at home to transplant into the raised bed once I've got rid of the Cos lettuce, and I was thinking of doing the same. It never occurred to me that it would be different rules for different plants, so thank you for the heads-up. Shall just bung them all out at the same time, and save myself some laborious tag-writing.

How many PSB plants would a family of four need? We do like the stuff VERY much.......I was 'advised' to get 4 calabrese plants for this season, looking at them growing ATM, I honestly don't think it's enough for us. Fortunately, we've lots more things growing to bolster things up, but we won't have that luxury when the PSB is ready. I'm not planning on growing any winter cabbage, nobody likes it except me, and we're growing hardy dwarf kale anyway........I was thinking of maybe finding the room to plant 8 or 10 PSB - if we have too much, it wouldn't be a problem to give it away to people, but I have no idea how productive it is.

If they survive the winter and the bugs and any other problems nature throws at us, you will most definitely be giving it away if you grow that many! Also the plants are ENORMOUS so think about space. I think 4 plants will do you fine - in fact half that amount would feed you all but I'd do the two extra in case any sucumb to black fly or caterpillar attack. Fewer plants also means less time on cabbage white caterpillar patrol, which seriously takes up some time - and you will need to do it unless you rig up some kind of butterfly netting!

Errr...
What's PSB?

Purple Sprouting Broccoli

OIC. Thanks. Not a huge fan of broccoli, 2B honest.

Growing Swiss Chard for the first time this year (it's only my second full year of veg. growing since the 80s, when I made an abortive attempt), I had fine plans for successionally sowing it, sowing in Marchm April, May and June. The March sowing (direct) failed to appear at all, and very little of the April sowing appeared either - just two plants, now reaching cut-and-come-again size. My final attempt was made in seed compost in a seed tray, and recently planted out, where it's still alive at least. Swiss Chard is supposed to be easy, but I found Chard 'ard! The varieties are 'Golden' and 'Sibilla', the latter a white-stalked variety.
Had similar probs with lettuce ('Cardinale'), which I also planned to successional-sow - third sowing now in peat pots in the greenhouse. I think I planted the first two out when they were too small, so I'm letting this sowing get bigger before planting out.
It was still flipping cold in March, and I think I failed to take account of the ghastly winter and cold early Spring we've just had - I mean, I know Chard is hardy, but there are limits.

I grow spinach beet (perpetual spinach) which is similar and that I sowed in early april - I've NEVER had a germination problem but this year was bizzare. Don't think they got watered by my housesitters whilst I was on hols and only one had germinated when I got back beg of May. Since then a few more popped up, then I was going to resow in all the gaps but then suddenly more appeared. So I've got one with 2 inch long leaves and a load of tiny seedlings but normally it would be pickable by now! I blame the wierd mix of no/very little rain plus too cold or too hot as the temps have varied wildly this spring.

I don't think anyone has actually said that if you want a succession of veg over winter, you either plant things that will stand a long time, such as the winter cabbages and kales, or you have to plant different varieties of the same veg., eg early and late PSB and cauliflower varieties have very specific timings. If you only need a small number of each, then having a succession of varieties is a bit of a problem/costly (although brassicas seed lasts for a good few years).
In terms of calabrese there are now overwintering types (eg. Aquiles), outside I think they produce stalks in June but we grew them in the polytunnel and they have produced from end of February until June. Whereas our PSB sown the same last September and planted in the polytunnel has only just sprouted!