it looks like you have a lot of grain runout in your last picture; I'd back it soon before proceeding further to avoid having a catastrophe involving those. You don't know when it might snap, it'd be safer to have a backing on it. So far, so good. Start long string tillering and go slow; if you take it off, remove wood, and put it back on to the same draw length, and it still has the same incorrect shape, it should be obvious not to pull further. Work out everything about the tiller before pulling further.