Having seen that this wiretapping is actually producing beneficial results, he would then be more inclined to keep it going so it can keep producing these results
Obama is bright guy but, Blackberry aside, let's not kid ourselves that he understands technology any better than the normal user. The national security apparatus is worth hundreds of billions of dollars a year and hundreds of thousands of jobs in the government, military, and private sector. You better believe they are skilled at scaring the shit out people, regardless of whether the threat is real or imagine nor the programs effective or not. A lot jobs, prestige, and profit statements depend on that ability.
Precious few people in Washington or anywhere else want to take on the intelligence community. There is very little political upside and a very dark downside. Outside of a brief couple of years in the 70s with the Church Committee, etc., they get their way eventually. And don't think for a second that in the back of their minds politicians, including presidents, don't fear there could be leaks about their girlfriends, "random" personal banking audits that turn up high priced hooker payments, a plane crash or a grassy knoll in their future if they step too far out of line.
With two wars, a collapsing economy, global competition, etc., it quite possible that even if Obama sees through the fear mongering he would conclude he doesn't want to deal with this crap.