Mr. Bush's campaign was supported by Mr. Cheney and the Reagan crew (Rumsfeld et al). Additionally, his opponent was Al Gore, one of the feeblest candidates in recent memory. For all the ammunition which the conservatives can bring against Mr. Obama, he has already demonstrated that he is a skilled campaigner. Bush was not campaigning against a sitting president, but Perry would be. Bush portrayed himself as a compassionate conservative, and while campaigning on traditional Reublican values of tax cuts and defense spending, he also portrayed himself as deeply concerned with the plight of minorities and the state of education in the nation. Perry is not likely to be credible on the compassion issue, he can hardly cut taxes further without precipitating economic disaster, and Mr. Obama has been quite generous with his defense spending. Finally, Bush campaigned in an era of fiscal high times, with Mr. Clinton having finally bullied the Republicans into balancing their budgets, while polls showed that people didn't feel burdened by their tax bills. Perry would have to peddle tax cuts and increased defense spending, if he chooses that route, in an era of fiscal starvation.
I don't think your analogy makes it. More importantly, it should be remembered that Mr. Bush was a minority president in his first term--despite all of Gore's weaknesses in the campaign, he still polled more in the popular vote than Bush did. Bush became president largely because the Supremes fiddled the Florida recount.