Which Ueno station?

We have rented a place in Nishi-Asakusa(2) area,our 2 children will arrive independently at Narita at different times. Do you recommend taking the KeiseiSkyliner to Ueno station, I saw on the map there are 2 station,one big one I assume is JR line and one smaller one label Keisei Ueno station,we want to be able to meet them at the station. Can you tell me which one the Skyliner stops and also is there a good landmark place at the station to meet?

The Keisei Skyliner will stop at the Keisei Ueno Station.

The main entrance of the Keisei Ueno station is not very big, so just the gates at Keisei Ueno is fine.

are the 2 stations connected via walkways? Would it be easier to come out on the Asakusa side of the Ueno station.

If you take the Skyliner it ends at UENO. When you exit the gates turn left. When you reach the street turn left again, walk around the corner, cross the street to the Ginza subway entrance. Asakusa is the 3rd station.
A better way is to take a regular Keisei train, not the Skyliner, many of them run into the Asakusa subway so there's no need to change. Ask the attendant on the platform which train to take.