So I managed to find a temporary fix for my problem. See I updated from Ubuntu 18.04, so not sure if this will help anyone updating from like 16.04, 17.04, 19.04 etc. Anyways the reason why I was having trouble with this is the fact that I have 2 keyboard layouts. I use an American and British layout. I am from the UK and always use the £ in everyday use. See, I have to switch layouts to use £ but then I forget to switch back to the original default layout, in this case, the American layout. At which point the super key stops working. I then try to get it to work for like 30 minutes to then only realise that oh wait I'm on not on the US layout. So I now use the English (intl., with AltGr dead keys)