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I haven't seen the headmans up close and personal, but if I were a betting man, I would say no. I can't imagine any full-length 300 header that gives decent starter room.
Yes, you can. It isn't fun but it can be done. The required tools list includes a prybar and some creative combinations of extensions. An easier solution would probably be the smaller starter from a later model truck. I think they started using the smaller one in 92 or 93.