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WiFi deadzones are easy to handle, you've already done some of it - just add more APs to your existing system. Inside and/or out. Helps to have a graphical signal strength monitor of some type so you can determine best placement. Depending on how full scale you want to go run a trench down the side of the drive and add an AP in the middle. You could maybe even go solar and just run fiber. After that, it would just be the transition from cell to wireless.
And yes, they do make pico cells that will provide a cell signal backed by your network connection. Unfortunately, I don't know if there is any way to lock them down to just "a few" phones (unless you want to be nice and supply neighbors with service....)
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