Not living in CT but do live in SA.
As it cant comment on the living in CT issue, i can chat about the schooling.
OP, have you considered if you are looking at private schooling or government? There are some very good government schools, but getting a place in those schools can be difficult. You will need to live in the area zoned for the school, and the houses in the best zoned areas cost a lot more. If you are looking at private, also be quite cautious too. There are a lot of fantastic private schools. There are sadly some dodgy ones too. There has been a lot of emphasis on how bad the government schools are so lots of homeschool type schools have been opened, and some of the cases i know about, they aren't properly registered, doing different curriculums etc. So just a head up there.
Ages 6 and 8. Your 6 year old will most likely start again in grade 1. This the first year of formal schooling. Yes they learn to read, write etc in this year which your dc will already have done. But, your dc may not be emotionally ready to be put straight into Grade 2. Your 8 year old would go to Grade 3. These are the foundation stage years. They stay with one teacher in a class, and she teaches everything. All this changes in Grade 4, when they reach senior phase (of primary which is Grade 4-7). They will have 4 or 5 teachers and move class at each period. It is a big step up from Grade 3.
Also, the CAPS curriculum is now taught here. It is not like the UK as if your dc do not pass each subject at the end of the year, they will not go up to the next grade. They will repeat that year. Each subject has its different pass mark, 50% is the pass mark for English and Maths. They will also learn Afrikaans at school. If they are at an English school, then it is most likely that Afrikaans will be the second language taught.
Not all, but most parents both work. Especially if your child is at private school as the fees can be quite high. After care clubs are plentiful. Many mums do work morning only, so they can fetch from school. Buses and trains are not an option. Few families walk, as mentioned previously.
Sport is very high up on the agenda here. Most schools will insist that the child plays at least one summer and one winter sport. They are usually done straight after school.
School starts anytime from 7.30-7.45am and ends between 1-2pm (the foundation phase usually come out earlier than senior phase). So usually the parent will drop the dc off at school on their way to work, so traffic is bad around schools, heading to highway etc. You notice a huge reduction in traffic during the school holidays.
Having children at school is a sure fire way to make friends imo. South Africans are generally very friendly people, and i have no doubt it wont be long before you are invited to someone's house for a braai
Cell phones and internet are expensive. We are way behind the times here, there is one company that does unlimited internet but you have to have a landline phone for this. Where i live, we have no landlines ( ) so i have to rely on 3g network for internet. This is the most expensive so we don't have unlimited use of it.
And you will have to have two cars. You will not manage, or should i say your will most probably battle with one car between you. Cars are a lot more expensive here, but if it were me, i wouldn't consider bringing your car here. There is getting it here, then the customs duty and the paperwork side of it can be a nightmare. I would sell it there and buy a 2nd hand one here to start off with.
If you can drive on your British licence here for a year. You do not need to go and buy one of those international ones. It is a waste of money. If after a year you intend on staying, you can swop your UK licence for a SA one. Or you could just go sit your test again here and keep both. Your insurance will be higher as long as you are driving on your UK licence though.
From what i have read, you have spent some time here already. So you know that our supermarkets are not like Asda or Tescos. We don't have the selection of things you may be used to, things like internet shopping haven't really taken off here like in the UK. A lot of folk I know still go and queue and pay their bills each month a the shops. Life is different in that way, you wont get your post for two weeks, the service for that sort of thing, just isn't the same .
And of course, how could I not say in here somewhere that CT has to be one of the most beautiful places on earth .