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Plus you'd keep your wits sharp trying to find low bucket roomettes continuously.
I'm pretty sure you could get a deal. Some kind of quantity discount, or maybe they would let you keep the same room, so you could furnish it. Maybe add a small galley.
 
Also, remember CBP counts all time in North America counts towards the 90 days, popping over to Canada, Mexico or the Caribbean doesn't reset the clock.

My most memorable Canadian customs stop on the northbound Adirondack was when CBSA kicked off a Brit, they took him off the train all I heard him say was "I was mistaken" when he thought going to Canada he was planning to spend just a few days there before flying back to the states would reset his 90 days ESTA Visa.

We Americans have the same time limit issue in the Schengen zone, with the UK and Ireland counted separately.
 
I'm pretty sure you could get a deal. Some kind of quantity discount
I find it extremely unbelievable that Amtrak would ever do such a thing.

or maybe they would let you keep the same room, so you could furnish it. Maybe add a small galley.
They wouldn't be on the same train for the 3 months, they would just be spending each night of those 3 months on the train. But theres no train that exceeds four nights, meaning every at least 4 nights you will be switching cars, and therefore switching rooms.
 
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