Your son only needs a guest pass if he plans to use any of the amenities.... rec centers, pools, golf courses. And, no, you don't have to escort him to any of these venues if he has a guest pass (and an accompanying photo ID like a drivers license).
If, however, you're going to keep him busy helping you unpack and setup house, then there is no reason to get him a guest pass.
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Maryland (DC Suburbs) - first 51 years 
The Villages - next 51 years 
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