Bush is a pragmatist who cares most about winning. Reagan was an idealist who was willing to be pragmatic.
Reagan took his own life and his family's life in his hands when he battled the Hollywood Communists who tried to run the Screen Actors' Guild. We now have a huge archive of what Reagan thought and wrote in his early days, long before he entered politics.
W. is not much of a thinker. He is much smarter than the Democrats allow, but he is a poor communicator, worse than his father. My biggest complaint is that he ran as conservative, like his father, and governed as a Democrat, like his father, trying to please the enemy while spiting his supporters.
Bush 1 used to say, "If you're so smart, why aren't you president?" That is typical Bush arrogance and explains why both failed as leaders.
That is really a misguided assessment. He's shown on many occasions that he is willing to risk his popularity and "winning" for what he thinks is right. He tried for SS reform - long considered the "third rail" of politics, because he knows we have to do it. He's stuck by his Constructionist nominees for the Courts (unlike Reagan who compromised on Sandra Day O'Connor). And he's still fighting to make his tax cuts permanent.
Those are all good Conservative positions. And if he manages all 3, he'd have to be considered as extremely successful.
You're right, he's not a good communicator - at least in front of a camera. People who have been in personal meetings give him rave reviews for those sessions though.