[BATMAN 300]'s batman's version of whatever happened to the man of tomorrow
Yes, it gives Batman a happier ending than just about any other "imaginary" Batman future story. Although if I wrote it, I'd have him bedding down passionately with Selina Kyle every night.
Miller's DARK KNIGHT RETURNS was out the same year as SUPERMAN: WHATEVER HAPPENED TO THE MAN OF TOMORROW, so I lean toward thinking of Miller's DARK KNIGHT as the equivalent treatment of Batman. But you're right in the more upbeat conclusion of issue 300 being a better comparison to "Man of Tomorrow".