Ah, the humble caboose: a place for the conductor to do his paperwork, for brakemen to keep an eye out for trouble and help with reverse movements, and a little home away from home for the whole crew on long hauls. They were largely phased out in the 1980s, as various improvements in reliability and automation made them redundant. They still get some use these days, usually during track maintenance and yards movements.
My grandpa was a brakeman for Union Pacific in the Walla Walla area from the 1950s until his death in the mid '80s. The caboose was where he spent most of his time, generally between Hinkle, OR and Ayer, WA, largely along the Columbia and Snake Rivers. I can't help but have a personal connection here.
I can't remember the last time I saw a caboose in action, but today was my lucky day! Around 12:30, while driving back to the studio on East Sprague during my lunch break, I heard a funny-sounding horn: nothing like a car or semi-truck, and too "small" sounding to be a locomotive. For you music nerds, the horn had two pitches, separated by an octave and a major 3rd...or a major 10th, if you prefer. I looked over to the Union Pacific tracks and saw a short train moving slowly in reverse, with the caboose leading the way! Being the train nerd I am, I flipped a u-turn and managed to snap a few pics as it crossed Havana going into the UP yard.
I did some research: this caboose, UP 25893, which has a bay window but no cupola, is a model CA-11 built in July 1979 by the International Car Company of Kenton, OH. It was one of a batch of 100: the last new cabooses ever built for Union Pacific. UP 25893 was one of the last seven of the batch, the only ones to have the slogan "I follow the leader" painted upon them. It's rusty, dirty, and well worn, but apparently still does the job.
Oh, a friendly word of advice to the gentlemen: don't tell the ladies you're into caboose pics. They might get the wrong idea.
If you're curious about the locomotive powering the train, it was UP 1483, which I've seen doing yard operations before. Interesting to see it hauling a BNSF boxcar: probably part of some interchange agreement for a local shipper.