My first New Haven layout was going to be set in Autumn 1948. I was able to purchase a public timetable for September 26, 1948. By sheer cooincidence, the Railroad Archives at the Dodd Center at UCONN in Storrs had a copy of the corresponding Employee Timetable.
So my initial inclination was to model the same period. The problem that arose is that the last steam locomotives on the Highland line left in January of 1949. Steam locomotives for New Haven modelers must be scratch-built, or brass, with few exceptions. Neither are an option for me right now, so I started looking at moving to 1949. I didn't want to model later than that, because I wanted to retain the original appearance of the DER-1 locomotives, and they were rebuilt from 1949-1951.
But once I started researching, I found that I could include the DERS-2c locomotives if I switched to 1950. In addition, Westerfield had the July, 1950 ORER available on CD-ROM. I also found out that I could get the October 2, 1950 engine and caboose assignments.
So now I was leaning toward 1950. The first non-alco road diesels were the DERS-3 locomotives (Fairbanks-Morse H16-44) and they were delivered starting in November, 1950. So I could retain an all Alco roster if I stuck with autumn 1950.
But things are never that simple. I have the Consist book for 1951. In addition, the DERS-3 locomotives were growing on me. I also learned that freight and passenger traffic was reduced on the Highland line in 1949-1950, but picked up again in 1951 due to the Korean War.
Well, I think you can see where this is heading...
Then I realized that the city itself did not change significantly through any of these years. The date on the layout will be determined by a combination of signs, billboards, automobiles, and the trains and timetables. Most cars found on the road at any time are not from the current model year, so that's easy to deal with. By planning to have a few "year specific" scenic elements that are replaceable on the layout, I can model a period of time, rather than a specific date.
I had always planned on autumn, since I figured I might as well model the New England foliage. But for the bulk of the layout there will be no trees. It's all urban. So if I plan appropriately, I can even swap out a few trees to change the seasons.
As it turns out, the last confirmed steam running on the Highland line was in November of 1948 on the Boston assigned trains 131 and 136. The New Haven reduced the Highland line from Newington to Plainville (through New Britain) to a single-track mainline in summer of 1954. So by using these as the defining events, the layout would now be designed to be accurate from 1948-1954. And when I get around to learning how to scratch-build steam locomotives, I can easily step back to 1947.
Right now, my operation focus is on the post-steam, but pre-Budd RDC car era. This sets my primary era as 1949-1953, with 1951-1952 as the core years due to the variety of locomotives and the increase in passenger and freight traffic due to the Korean War.
This also works well historically in other ways. The management of the railroad changed significantly 3 different times in this period. The first was in 1947-8 when the railroad came out of bankruptcy. In August of 1948, a former director of the railroad, Frederic C. Dumaine, Sr. took control of the railroad in a proxy fight. He believed in cutting expenses, and greatly reduced the maintenance of the railroad. After his death in May of 1951 his son, Frederic C. "Buck" Dumaine, Jr. steered the company in the exact opposite direction, increasing service and maintenance. He remained in charge of the company until Patrick McGinnis, a partner of his father who helped in the takeover of the company in 1948, did the same thing and took control of the company in April of 1954.
In essence, I'm modeling two different eras: The "dirty" era, of Frederic C, Dumaine, Sr. when locomotives, freight, and non-revenue equipment will be heavily weathered; and the "Buck" Dumaine era when equipment is well maintained. The primary era will be the second.