In applescript how do i get two different things to repeat at the same time
You could take advantage of the fact that 44 is evenly divisible by 5.5 and use an inner and outer loop:

repeat
    keystroke "i"
    repeat 8 times
        keystroke "o"
        delay 5.5
    end repeat
end repeat


Note that for the keystroke command to work, you need to be in a tell block for the System Events application.