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Marc S.Cuban cards are legitimate cards. I was actually very surprised by warshawlaw's comments. I never really considered that there may be many of these still in Cuba. I've always grouped them sort of like the Venezuelan Topps cards of the 1960s -- hard to find because people collected them in different ways, with few surviving high grade examples. I know that a lot of the major autograph dealers have made their way to and around Cuba (through whatever means) to acquire significant collections of autographs of Cuban players. I would have thought that perhaps the cards would have escaped, too.
As for umpire cards -- I typically view the 1955 Bowmans as legitimate to collect for a HOF collection, but I don't feel the same way for the T&M Sports Umpires. Personal preference perhaps.
As for managers who were players -- I typically view their first playing card as the one I would collect. I don't know if it makes the most logical sense, but perhaps it is just an excuse to hold an older card of the player. Sparky Anderson was a horribly player for the Phillies for his short stint in the late 50's, early 60s, but I would much rather own his 1959 Topps card than a 1989 Topps manager card.
I also think that some of the executive cards issued by Topps and other in the 1950s also make my list of "legitimate" HOF cards.