1) Don't ever let the words "I don't care about the very poor" come out of your mouth in that sequence, unless what you are saying is "Season 4 of Jersey Shore? I don't care. About the very poor, though, I care a great deal." Then and only then should those words be said in that exact order.
2) An endorsement from Donald Trump should be treated like an endorsement from Charles Manson. Who on earth is going to give you their vote because of that endorsement???
3) Nobody--except for the economically ignorant--will fault you for having made a fortune legally, and paying only as much in taxes as you were required by law. But you should realize that your relatively low tax rate conflicts with your message that taxes for wealthy investors--like yourself--should be reduced further when deficits are out of control, and voters will resent that message coming from you. If anything, you are in a better position to argue for tax code simplification so that ordinary income is taxed the same as capital gains.
4) Seriously, don't wear jeans. They look out of place on a rich guy with newscaster looks.
5) You don't really need to use negative ads against Gingrich and Santorum. Santorum can be defeated by just asking voters to Google his name. Gingrich can be defeated by just letting him speak, and remind people that he's Newt Gingrich.
6) Nobody believes for a minute that you genuinely want to use the power of the state to prevent gays from marrying one another, particularly considering you adopted this position for the first time in 2008. You might as well take a stand on principle here.
7) Opposing everything Obama does--even when it's hawkish moves in foreign policy, tax cuts at home, and budget cuts that would all otherwise be cheered by the GOP--only makes it look less credible. Give him credit now and then, so that what you actually do oppose will have greater weight.
8) With today's job numbers--unemployment down to 8.3% and a monthly gain of 250,000 jobs--it's looking more and more like Obama's getting re-elected. Win or lose come November, you at least don't want to go down in flames as embarrassingly as your last two Massachusetts predecessors (Messrs. Kerry and Dukakis). Best to take the above advice!