Here's my Bay Bayou and Gulf (BB&G) transfer caboose right before I rebuilt it:
(you can see the damage to the roof support on the far side)
When the shops were chopping down the full sized caboose to a transfer length, the crew requested the roof be left on full length for protection from the brutal Gulf sun, and the frequent summer thunderstorms... someone brought some lawn chairs to eat lunch out on the deck, and then they put a grill onboard for cooking said lunch... also Bubba always brings Ol' Blue to work. He's a good dog, and like to watch the rear...
In the rebuild, I beefed up the roof supports, painted the roof gray for cooling purposes, added an A/C unit on the roof, and installed a muffler for the under-slung generator.