1927 was the 20th Anniversary of American Flyer, but represented less than half of the variations of prewar tunnels. I should note that I am only covering prewar tunnels through 1937, as that is the era I collect.
In 1927 American Flyer still listed the 4255 and 4256 tunnels for standard gauge, but their O gauge offerings changed to
241 - 8 inch tunnel
242 - 10 inch tunnel
243 - 14 inch tunnel
244 - 16 inch tunnel
The tunnels still looked somewhat crude and I should note that the 1925 through 1928 tunnels all feature what I would consider more of a flat, non-glossy paint.
The tunnel below is a 243 tunnel that came in a boxed 1927 Bluebird set that I purchased from the original owner's estate, Side A
Side B
End
I have just discovered that this tunnel is the 244 16 inch tunnel from 1927. There is a photo of Billy's layout at the beginning of the 1927 catalog that shows a large tunnel with the road and building orientation similar to this tunnel.
I don't have any other Tunnels that I can verify to be from 1927.
NWL