Pinellas was won by Al Gore in 2000. I think the GOP recovered with Jeb in 2002 but don't have any stats. Hillsborough is more Republican than Pinellas is nowadays.
Orlando is the center of the insurance business in Florida. Maybe some insurance people aren't so bad after all.
I do not know what paper is in Orlando - but in Pinnellas most people read the St. Petersbugh Times. Which I believe is owned by the New York Times. This may help explain the bias in Pinnellas.