A semi-comfortable spot for the head-end brakeman, I'm guessing, to watch the train. Some of the older European train cars seemed to have brakeman doghouses everywhere.
On the helper/caboose subject, I think there were rules for older wood-underframed cabooses. The helpers had to cut in ahead of them for obvious reasons.
No problem with the steel-underframe ones, although thinking about all that power squashing your ride would still be intimidating Ah reckon.