I think there's another reason why this wouldn't have worked for Owen
HHH was known for his Blue Blood and DX gimmicks.
Owen Hart was known for being "Bret's younger brother", Part of The New Foundation, The Black Hart, Part of the Nation and The Blue Blazer.
Owen had gone through A LOT OF CHANGES and I think YET ANOTHER GIMMICK wouldn't have worked for him. How can an audience take a character seriously who has had a whole lot of gimmicks placed on the same character?
Its a simple reason but that's why I believe it suits HHH more than Owen. Granted, the reason isn't a degrading factor if the question was something like "Would it have suited Owen Hart or Highlander Robbie more?" because of course, Owen's a superior wrestler. But with these two individuals, it does become a factor.
