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Although a 26-27 is wider, it is harder to get into than a 1925 or earlier. The problem with the 26-27 roadsters (and tourings) is the cowl is much deeper (longer-front to rear) which severely cuts into the cockpit area. There is also a gas tank under the cowl which doesn't help the space situation either. Also, the distance between the top of the seat to the bottom of the floor is shorter on the 26-27s, so, if you are long legged, it is really uncomfortable. You sit much lower in a 26-27 which is not good for vertical leg room.
While the 1925 and earlier cars are narrower, you sit like you would in a normal chair, meaning, your legs don't have to spread forward and get tucked under the cowl.
I have had both and since I am nearly 6 foot tall, the 1925 and earlier cars are much, much more comfortable and much easier to get in and out of.
(Hope this description makes sense!)