For number 2, I am sticking with Phil Jackson
I am going with Phil Jackson. It's all about making the most of the talent given to you (it's not greatest GM of all time -- yet) and Phil won multiple titles with two of the most different teams ever to win.
First, he took that Bulls team with no center and good but not great PFs (Ho Grant and Dennis Rodman were terrific role players but not dominant bigs) that had never been able to get over the hump and won 6 titles with it. Yes, MJ and Pippen were terrific players but in the history of the league, no one has ever won with centers as weak as Cartwright/Longley . . . the only teams that are close are the Barry led Warriors team (Cliff Ray and George Johnson), possibly the Sikma led Sonics (very good player but probably won't ever make HOF), last year's Celtics (though Garnett was the dominant big in the league then) and the Pistons (either Bill Laimbeer or Ben Wallace -- both great defenders/rebounders but not stars). SA used Duncan as a center once DRob retired or they would count too.
Second, he took a great center led team, the Shaq/Kobe Lakers, and juggled the egos of two of the bigger prima donnas around to multiple titles (not that Jordan and Pippen weren't tough egos to build a team around too in their own prima donna ways).
Auerbach had Russell, and Russell actually was the coach on the most amazing run of the great Celtic dynasty. The next closest dynastic coach might just be Pop.