are school onside with ipad going in? this would be a good way forward, ptoentially. dd1's ex-school were fab at communicating - great home/school book, always there for a chat or email etc.
btu I still sent in additional stuff because dd1 could not fully answer questions about what we did at the weekend etc - so photos on ipad, holiday scrapbooks etc - to go through together with tutors, and then she could comment more easily.
if school are likely to not want to, could you maybe link it to learning targets? ie I use the OU Our Story app with dd1 - I upload photos, add text, and she reads the story I have made up (using key words, high frequency words I know she is currently learning etc) - would this be possible for your ds? then it is less about home/school communication and more about learning targets, but the home/school communication gets done also.
I asked school for a folder of pictures of dd1 at school doing various activities to use in this app, and they obliged happily. you could maybe ask for updated photos once per half term?
otherwise I do just send in new picture folders on her ipad, but not sure how muh they get talked about.
I do a holiday scrapbook each time we go away too - add photos, and write it as though dd1 & 2 have written it ("today we went to the beach. mummy got sandin her shoes, and daddy fell over paddling" type stuff), so it can be read with dd1, and she can comment on it. this provides the main gist of the holiday, with picture support, and leaves room for dd1 to comment on her favourite bits too.