I could help you, yes. You have to go down to the bottom of the screen when you reply, and hit the little icon that looks like a picture, underneath the emotes. Are you replying from your phone? Because I don't think it shows up on there. You could also upload it somewhere like imgur, and then just post the URL
It does work on 9.3.3. I have it on my iPad right now. You have to go into the settings and enable the hack from there.
I'm not entirely sure, but you could either create a symbolic link pointing to the user applications folder, or it could be that your permissions are screwed up for that specific folder plus everything in it.