Today I learned about the American Association of Private Railroad Car Owners (AAPRCO)… I was going to say this might be a “bucket list” item, but now I think the bucket would have to be a lot bigger than anything I could ever anticipate dumping. But, drooling and dreaming are free, so I though I’d share. 
Ive chartered cars in the past for day trips. It’s a matter of getting enough of the right folks to chip in.
If that Powerball number ever comes in, there will be signs 
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Here’s a 2-day luxury ride, ~$5k per couple, only 16 seats available!
https://traintrips.biz/1-fall-colors-private-rail-car-adventure.php
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I’ve often thought that we (LSC) should charter a caboose on the Cumbres and Toltec.
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During many steam train (and diesel) excursions based from Roanoke, VA, I served as a “car host.” Got the ride for free because I was working as a volunteer. The job was similar to a flight attendant. I have even served boxed meals on occasion, and helped folks get on and off the coaches. It’s not terribly exhaustive, but you get to meet a lot of nice folks and have a good train ride.
Regards, David Meashey