HELP-WDW pro to DL in 2 weeks...1ST TIME EVER!

I don't know if I'd say that. LT is quite a popular nightlife spot nowadays. I'm looking at Yelp and it appears there are literally dozens of businesses open until fairly late on a Monday night. Most restaurants are open until at least 9pm, many until midnight or later.
I guess it depends where. The area on the eastern part by the court house and Music Center is pretty dead that late. Keep in mind they're leaving Anaheim at 7pm or later, so arriving 8pm or later. I've been to some clubs there, like the Edison and you don't see families out and about. It's not unsafe to be out front, but it gets a little sketchy walking back to the parking lot. There might be more on the western end. I'm not really sure of the boundary, or where the hotel is. I still wouldn't drive up that late and expect to find an activity for a family with a 10 year old Monday night.
 
Technically the Edison isn't in Little Tokyo. That part is commonly referred to as the Historic Core/Old Bank District and you're right that area is can be a little desolate on a weeknight. The main part of LT on First St towards Alameda is where all the action is and is quite lively. 9pm would still be considered early is these parts.
 












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