The Villages is using the wrong kind of card for gates. The current read range for a Villages gate card is about 2 feet. A real gate pass is UHF and has a read range up to 15 feet. You could leave a UHF card inside of a little clear plastic sleeve on your windshield and it would work from a distance.
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The big square grey readers have been able to read UHF since about 1987 I believe. So if they just started issuing UHF cards it would make everyone's life easier.
EDIT: issuing UHF cards would of course just be the first step. The cards would need to be dual technology to work with any old readers that don't have UHF, and then all new readers purchased could be UHF capable. Then slowly replace older readers. Instead of doing it all at once.