I may have bad information, but I have been told that the developer collects a percentage of all sales in the squares. If we are talking 10% and we assume that on an average night there is 2000 dollars spent per square or 5 dollars spent by 400 people as a result of increased traffic from the entertainment which is likely a low estimate, he makes 200/day extra. I don't know how the alcohol sales, and the market night sales figure in that. With two squares in Sumter county that is 400/d times 350 with some days cancelled thus about 140,000 in additional income. If my numbers are off, or way off, make whatever adjustments are needed but it seems that he profits from the extra traffic. This does not take into account the marketing value or the rental of stores value. If you have any question as to whether entertainment increases the shopper traffic in the squares, just compare the crowds daytime vs evening. Looking at the Sumter county website, it seems the Tourist Council gets its money from the 2% tax on rentals/hotels. It then spends its money 40% for event grants and 60% for capital improvements. According the Council's online grant application the amount available is determined by the number of beds which are occupied as a result of the activity.
http://sumtercountyfl.gov/DocumentView.aspx?DID=1844
Interestingly the language of the rules says the money from the county must be matched 50/50 by the grantee. And the grantee must be a non-profit. However this contract has the county providing 60K while the Vescos are providing 50K. It would be interesting to see the application and the reports which are required from the grantee showing how they spent the money. I have emailed the country asking where those documents can be seen online. So the money is coming from the occupancy tax not the homeowner.
While there may be more legalese somewhere, it is not clear how the Villages qualifies as a non-profit nor why the 50/50 rule was not enforced.