While I cannot answer all of your questions, virtually ALL of the roads in The Villages are county roads, as for the gates, these are usually installed to control traffic at golf cart crossings. THIS IS NOT A GATED COMMUNITY. While I am not sure of all of the arrangements in Marion and Lake counties, the portion of the villages in Sumter county are county roads except for the villas locations, where these are private roads.
Also, Google Earth has a "history" function that allows you to go back about 2 decades (or more) to see that aerial photos for decades ago, this might help.
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Pennsylvania, for 60+ years, most recently, Allentown, now TV. 
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