Great topic.
I am 56 years old. I was HO 1971-1980. Left hobby in high school.
1998, my parents moved from their home about 5 miles from my home, and all my HO stuff and anything else I never took when I moved out years prior ended up at my house.
I declared "I'm going to build a Lionel train layout." Start of glory days.
Went to a LHS on Oakton Street here in Chicago, Skokie to be more precise (long since closed, I think). Got a Santa Fe GP9 set with a 1033 controller, basically an oval shaped layout and a switch. Still have pretty much all of it. Put together the benchwork frame of my layout using all my HO benchwork.
Bug bit me. I found out about TMCC - had to have it. Sold all my old HO stuff to a hobby shop in Park Ridge, and got a board for my GP9. I ordered a bunch of track and switches and well of course other things from a internet hobby shop in NY (guy was named Henry).
Christmas morning, 1998, I unwrapped all my stuff and vanished to the basement. Hours later I had two ovals and a figure 8 in the middle. One of my engines was a Lionel B&O GP9. Also still have. While my straight track wasn't so straight, it was OK in my book. I discovered Mike's Trains and Toys in Morton Grove and Chicagoland Hobby.
Subscribed to OGR and CTT, discovered eBay for train purchases. Reading these two magazines, I discovered you could have a layout built. Oh now that made a ton of sense for me.
In 2000, I had Layouts by Cardiff build my layout. Simply wow. I really liked TMCC so was pretty much sold on Lionel, Atlas and K-line. MTH not so much. Catalogs coming out were such a great wow to me but then realizing the time from catalog to a hobby shop was an eternity. I could look at the catalogs for hours, and actually I did.
DCS comes along from MTH and I had to have it. PS2 engines - great. More opportunities to buy. I am finding I have a problem. I am getting a lot of stuff.
In 2004, I moved to my current house, old layout torn down and semi started from scratch. My current layout was done in 2005/2006 ish time frame, and runs TMCC and DCS. I favor TMCC equipped engines at the time because I struggled with DCS finding my engines.
In the past 10 + years we have seen the Cab2 system come out and DCS WiFi as well, also saw K-line and Weaver vanish. Still feeling pretty golden to me. MTH announces going out of business, and there is a frenzy of activity to buy stuff. My one remaining hobby shop Chicagoland Hobbies is going to close soon.
I really love the new technology and the craftsment that exist in this hobby. Had a B&O Lionel steam engine weathered along with a matching passenger car set, thank you @MrMuffin'sTrains and Harry Heike. Just wow.
When my trains work, and for the most part they do, I feel very much I am in a golden age.
John