While not in your region of interest, the State of Ohio passed a caboose law in 1913 that affected every railroad operating in or through that state.
It specified a caboose used in main line service in Ohio must have a frame length of at least 30' and ride on four-wheel trucks.
In compliance, B&O designed and built their I-1 class cabooses in 1913, which also had steel underframes.
The better known B&O I-5 class caboose was a 1920's development of the I-1.
Cabooses not meeting Ohio requirements were moved to other locations and downgraded to branch or terminal service.
The earlier B&O K-1 class four-wheel cabooses built between 1878 and 1913 were 23' long overall with wood under-framing.
Several survived into the 1950' in terminal service with some getting replacement steel under-frames.
On the B&O the K-1 cabooses last worked to about 1953 on the B&O Chicago Terminal and the Staten Island Rapid Transit (B&O New York Terminal).
On the SIRT the K-1 class worked interstate freights between Cranford Jct. in New Jersey and the Arlington and St. George yards on Staten Island, from 1890 to 1953.
They were replaced by I-1 class cabooses built in 1913. The assigned K-1's were burned for scrap later in 1953.
C-587 seen here in 1940 at St. George, has a replacement steel underframe.
The PRR in 1913 also had four wheel cabooses working in Ohio. These had longer underframes.
PRR converted some by putting pair of trucks under them in place of their two wheel sets.