I'm more inclined to say that is the nature of the football.  The FHSAA record books are littered with many examples of this scenario throughout the decades.

It would take a smaller county that has $$$ and values the educational system. Can’t have an overabundance of retirees, whose interests do not lie in public education. Collier, Sarasota, etc wouldn’t work because retirees wouldn’t vote for higher taxes to go toward public education.    Okaloosa, Bay, Walton, St Johns come to mind. They would have to vote to make property taxes around 3% or pass a substantial sales tax (penny tax or more).    As far as panhandle coaches pay, Okaloosa used to combine HFC/AD to make it an admin position and they were paid as such. They recently removed the requirement for HFC to also be the AD, allowing other coaches to be the AD. It gave women more of a chance to be AD. When they redid their HFC pay structure, they made it so the minimum pay is 75k unless your experience/degrees take you over that. I believe Walton still combines and Bay doesn’t combine but has a great setup for HFC.    Teaching pay in the panhandle isn’t great. They meet the new state minimum but, historically, many teachers are military spouses whose pay was the second income, so there didn’t seem to be a major push for higher wages.    Walton county has recently raised teacher pay and advertised across county lines to poach teachers, which is a good move on their part. The academic side of schools shouldn’t function like a business as we have to provide for all students, regardless of their circumstances, but administratively schools would do well to function like a business. Pay more, attract and retain talent, COMPETE.  The bottom line is an entire county has to value education and want to make an investment in it. Because if the size of the districts, it’s hard to get a majority on that same page. 

Winter Haven has had some success recently, especially in basketball the last two years. But this year they are atrocious in both sports. 

in the large metro counties, with 20 plus schools, no chance it could happen.  but im pretty sure there are counties that have less than 10 schools and it could happen.  no clue what it would take to take a small county with 5 schools and pull off an ISD model and give teachers an extra 10k to work there and pay coaches like kings.  Im sure some of those small county like that the football could not be nearly as good(or already be good, idk) or the actual resources to pull off such a feat would be nearly impossible at the specific county school district level.   it would only take a few of the countys to do it and get a major pull from a larger county of teachers to get others on board. I will say, and I think im talking right, but doesnt many of the panhandle schools pay their teachers and coaches quite a bit more?  some of the head football coaches I thought were paid as administrators? that would be a step in the right direction at each school, or just pay the Head Football coach as an 11/12 month employee.  99% of them work year round anyways, IDK what any of them make per month but if it was 5k a month or 6k a month, wouldnt that be what the coaches want anyways?    

Hopefully this will make sense. To put your situation in TX terms, the Palm Harbor area of Pinellas would likely be its own independent school district (PHISD).  That is a huge distinguishing factor that separates TX schools from FL. In this setup, PHISD sets forth policies and infrastructure in a way that reflects their community’s values.  Because they are an affluent area, ~3% property taxes bring in an immense amount of money. That allows them to attract and retain high caliber teachers/coaches/administrators by paying them well and providing them with the resources they need (one of the noteworthy things about TX is that teachers do not complain about pay and there are FAR more young people going into education because it is a viable career due to the pay). The other benefit of this is that when PHISD pays well, similar districts like “South Tampa ISD” or “Venice ISD” must follow suit to compete for high quality workers. For less affluent/city areas that may not have the high residential property tax revenue, this is taken care of because skyscrapers and commercial real estate are taxed at the same rate (which is why TX oil towns have great school districts…an Odessa oil tank is taxed just like a Highland Park mansion). So PHISD can pay staff competitively at their discretion. They can also pass municipal bonds for capital projects that reflect their community’s values. They want an 8,000 seat stadium, new fine arts building, turf installation on practice fields, baseball and softball fields (happens more than you think in TX), put it to a vote and get the community to agree to it. The smaller scale of the district allows you to get things done that are important to that community, not be held back by the differing interests across the county as it is in FL.    The smaller school districts make districts compete and race to the top, instead of what we do in FL which is to do legislative gymnastics to get by paying teachers/fund schools minimally because there is no incentive to with no competition for personnel and families. Districts complete for families to live in their district just like they compete for teachers and staff. In your example where Palm Harbor has support but others do not, the TX model would make it so that that area is not bound by the other areas. It really is a great setup by can’t happen in FL due to state law mandating each county be its own school district.