Far be it for me to offer campaign advice to John McCain, but I've got to say that I am extremely puzzled (and rather delighted) by his seeming willingness, perhaps eagerness, to antagonize voters in Florida. 
Today, speaking to Republican donors and oil moguls in Houston, McCain called for allowing offshore oil drilling. This is high risk in Florida, where the population and elected officials of both parties overwhelming oppose lifting the drilling ban. In a state where tourism is a major part of the economy, and where the 1,300 miles of coastline and beaches define the geography and identity of the state, people are understandably not eager to gamble with a repeat of the Santa Barbara oil spill of 1969.
But that isn't all:
McCain is opposed to the creation of a national hurricane insurance fund -- something high on the agenda of Gov Crist and voters living in this hurricane-prone state. How ironic that he gives speeches condemning the Bush response to Katrina and Rita, but opposes something the federal government could do now to give some peace of mind and practical support for people living in Florida, Louisiana, Mississippi, Alabama, Georgia, South Carolina, North Carolina, Virginia and Texas. Maybe he was too busy chewing birthday cake with George Bush a few Augusts ago to understand why people in those states need and deserve this insurance.
Of course there is also his well-publicized vote against an appropriations bill that would have funded Everglades restoration -- despite the fact that Republicans and Democrats alike fought hard to get this "earmark" into the omnibus bill (which was the only practical way to get the measure funded). John McCain stood with George W Bush (who vetoed the bill) -- but it became law anyway when the Democrats in Congress (and some sane Republicans as well) overrode that veto. (McCain claimed that he in fact is in favor of the Everglades plan - going so far as to do an Everglades photo op to replace his vote against -- so he was "against it before he was for it"?)
And John McCain is stuck in a rabid anti-Castro time warp that is popular with a dying generation of original Cuban exiles, but is increasing questioned by younger Cuban-Americans, recent exiles, and people who still have family on the island. By adopting a hard line embargo position, siding with the Bush administration's refusal to loosen rules on frequency of family visits and the amount of remittances to family members still in Cuba, McCain provides an opening for Obama to make a significant dent in the formerly solidly Republican Cuban-American vote in south Florida. Witness the friendly reception Obama got when he spoke to the Cuban-American National Foundation recently -- a sign that many people realize that 40+ years of non-engagement and the embargo haven't succeeded in changing the government in Cuba. If Obama can improve on Gore's 20% performance among Cuban-American voters in 2000, it flips the balance in Miami-Dade and the state. And with three strong Democratic candidates challenging the 3 south Florida Republican members of congress representing predominately Cuban districts, there is every reason to believe that Democratic total there will improve significantly.
And last, but certainly not least, let's not forget his support for Bush attempt to privatize Social Security, and his own contradictory confused statements on the subject. McCain doesn't get that in the YouTube age, you can't just pretend you didn't say something when there is video of it available. Senior citizens have always been (justifiably) frightened of politicians playing games with the income many of them barely scrap by on. In a state where the senior vote is as large and organized as Florida, this could be the issue that Democrats will be able to use to remind older voters that McCain may be old, but he is no friend of the elderly.
Of course, in addition to these issues with particular resonance in Florida, voters there will also be voting on the Iraq debacle, the tanking economy, the growing income disparity in America, global warming, and other issues that work in Obama's favor.
None of this is to say that Florida is a slam dunk for Obama -- far from it. Democrats will have to work like hell to win here -- there is such a large Republican voting base that they will be highly competitive there, Maybe John McCain is figuring that he can coast on the time he spent in Pensacola and Joe Lieberman trying to scare south Florida's Jewish voters --- but if he keeps doing things to alienate Florida, it just won't be enough. 
There has been much buzz over the last few days about the Obama campaign's position that he can win without winning Florida by changing the map in other places. But let's be absolutely clear -- McCain has virtually no chance of being getting to 270 if he can't carry Florida.