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I'd also like to chip in with the go with the DSLR to start with - he probably already has something that could be used. More money can then be spent on the rest of the gear, especially the mount (go GEM/CGEM), since that's where a significant amount of the learning will be (besides processing, but I'm assuming since they are an experienced photographer, that side of things should not be too hard).
I wouldn't bother with a Polemaster personally, but use other cheaper solutions - plus ensure the learning process covers a number of techniques for PA.
I agree with the OAG path.
And because I'm suggesting a DSLR, I think a reflector of some type rather than a refractor might be better for overall colour.
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