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Thanks for the replies. I just want to make sure I have this right. In attached image red is bus loop which can be a mess and teal is where we could do pick up. I don't have a problem with going through security again but don't want to have to deal with the main city walk entrance security. That tends to be a cluster bleep from my memory. Once a day is enough for me.
The red path in that image is a backstage road, if I'm not mistaken?
I believe the bus loop you're referring to is the one by the main parking garages? That bus loop used to include uber and pickup/drop-off, but a few years ago they changed it to limit congestion. The new pickup/drop off is at one of the parking garages (did my best to show it in the picture below). For that reason, I'd recommend walking to the Hard Rock Hotel (green line below), and having them pick up your son there.
The only caveat is that you'll want to be at the hotel before their car arrives, as the hotel doesn't want tons of cars sitting there waiting for guests.
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I can wholeheartedly recommend Bort's suggestion, however with Bort's map that route goes through the pool area which does have a gate that requires a hotel key to access. If you don't have one, you just follow the gardenwalk path a little further to the big open yard/boat launch on the right and enter the hotel from there. Inside it's pretty much go up the main stairs to the lobby and exit.