If you dont mind venturing to suburbs, Planet Bounce in Tanger Outlets (Washington) is open til 7 pm. Fun Fore All in Cranberry is a nice place if they like arcades, and they have other outdoor activities as well though I'm not sure if they're open when it's cold.

South Hills Village has a store where you can make your own slime, Build a Bear, a big candy store, and a movie theater in the parking lot if there are any kid movies out right now.

Primal Pigment looks fun but kinda pricy.

Crowne Plaza hotel near South Hills Village? Or maybe 1781 Club (old Scenic Valley golf club) in Finleyville

Their website says they have an all-day breakfast menu.

Bethel Park, possibly

It's not gated, but maybe something like Southpointe in Canonsburg would fit what you're looking for. Agree with others that I've never really seen/heard of any gated communities in the Pgh area

Bartram House? First Watch near South Hills Village, or the new Waffles Inc. in USC

1. A few dollars or maybe 10% because I used to be a server and appreciated when people tipped on takeout orders, so I try to do the same when I can.

2. Usually 15%

3. 20% at least

CCP is basically UPMC's network of pediatricians, so they're massive and have locations all over the Burgh. What I like about the McMurray and Castle Shannon offices is that they were, until very recently, an independent practice called Pediatrics South, and their doctors has all been with the practice for many years. Unfortunately they took a huge financial hit during covid and ended up being bought out by CCP/UPMC, but the doctors and staff mostly stayed the same and continued business as usual with a different name.

McMurray location may be too far but the Castle Shannon office could work. It's south of the city.

What area of the city? I like Maya Goldin or Amy Gosling with CCP McMurray/Castle Shannon