In fairness to all the mowing guys out there, while it's true that they shouldn't be racing around your yard, they generally do a good job, have more knowledge about your grass than many "up north," and try to be conscientious.
My guy has been doing Villages yards for nearly ten years; mine for more than five. During the winter, no more than every other week; this past winter he skipped several weeks in a row, as the grass (St. Augustine) was sooooo stressed. In season, once a week, but he's sometimes missing a week here and there because the winter was so hard on the grass and it is now so dry that it's not growing as it should.
Yes, fuss and holler if they tear up your lawn, but I think you can, for the most part, trust their knowledge. That said, I'd avoid anyone who offers you a monthly deal of less than $35, because I don't think that's reasonable.
SWR