I was able to track down one of the oldest sets I was looking for, and now I can show it to you!

This is from the very early days of 1.2.3, with the box saying it's from 1992, and other sources saying it's from 1993. Just a few years after the launch of 1.2.3 in 1990! This set was sold individually, or bundled with a railroad set. I already owned a later train set I wanted more, so I had been on the look out for this "sold separately" set. The person who sold it listed it for a very reasonable price due to him running a variety shop that didn't focus on any one thing. I'm very happy to own this set now, and it's going to be one of the few sets I keep the box for.
This is such an old set that it features something not seen on more modern sets. You can lock pieces in place on a grid similar to Lego so the pieces don't slide around! It's very cool, and works great for a set like this with lots of loose pieces.

In this example, the father is saying
"Here comes the train!" and enjoying how excited his daughter is. Meanwhile the mother anxiously looks at the clock as the train is running a little behind.
"Try to be more serious dear! We might miss our flight!" "Flights are always delayed, we have plenty of time!"This particular setup for the station is more concerned about keeping the clock and luggage safe from the rain.

In this setup, the husband gets ready to load the luggage as the train arrives. The daughter (who is waiting very patiently) is informed by her mother that it's time to get ready. In this particular layout, the station is more concerned about keeping its passengers safe from the rain. The clock is waterproof!

Another passenger arrives at the last moment to climb aboard!