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I'm not sure I agree that Lee and Eastwood are more similar than different. Eastwood's brand of filmmaking is heavily influenced by John Ford and classic Hollywood cinema. His style is largely invisible, and his films tend to feature tight, clearly told stories with well-defined protagonists. Lee, on the other hand, is more influenced by the 1970s generation of film-school mavericks, most obviously Scorsese and Van Peebles. Lee's style is experimental, self-conscious and narratively diffuse, and unlike Eastwood Lee works in a wide variety of genres, including documentary. Both have secured a place in American film history, and both are heavily influenced by music (though in very different ways) but beyond that they don't have very much in common.
I also doubt Lee would have made a better film of MIDNIGHT than Eastwood, since Lee's track record with gay and lesbian characters (cf. GET ON THE BUS, SHE HATE ME) is so abysmal.
