Robert,
Here are a few of my layout's scenes that relate to my life or my life with Sylvia. After you look at these, you'll probably have a dozen ideas how to incorporate similar memories from your life onto your layout.
My 20 years in the Air Force couldn't go without "mention" on the layout. Here's the south end of "Liberty Air Force Base" complete with a flagpole flying both the US and Air Force flags. (This is the new Lionel flagpole with LED lights. I pulled some graphics into PowerPoint and created the AF flag to fly under the US flag.)
Oh, that's right, the nitpickers always want a prototype for things on a layout. Here you go, nitpickers, the prototype is right on our front lawn where the US and AF flags fly 24 hrs a day including spot lights at night! 
Twenty-some years ago when my kids were in Sunday School, I would sit in front of 7-11 having a coffee and reading a newspaper. Well, that explains this structure... You should have heard my daughter laughing when she saw it in the very back end of the layout. BTW--notice the cannonball light? That did not come with the structure, but it works well for lighting up the sign.
I love blues music and have made the "pilgrimage" down to the Mississippi Delta to see all the major "blues history" sites. Sylvia and I have also been to Beale Street in Memphis including the Hard Rock Cafe. Those experiences led to this scene of our Dalmatian, Mick, listening to a bluesman playing the harmonica outside the Hard Rock Cafe on our layout.
(Prototype note for the nitpickers: Mick's collar in real life is red. Sylvia painted this red one on the Dalmatian figure "so it'll look like Mick's!")
