Originally Posted by septimusjm
You know, I've only upgraded to sleeper while onboard once (FL to NY), and it was easy, cheap, and the conductor was exceptionally helpful. It was also after midnight when I boarded the train. Maybe I shouldn't generalize too much from that experience.
At least to you the customer, it should be easy, and it’s really not a huge chore for the conductor either. Plus the conductor and/or assistant conductor should be helpful not only with upgrades, but everything. However, just like any hotel or airline being discussed on these boards, Amtrak sadly has its fair share of lazy and sometimes indifferent workers. There are even a few who are down right rude, although I've only met one during my 50,000 miles on Amtrak.
On the other hand, Amtrak has many exceptional workers who take pride in what they do, along with a bunch who at least do their jobs properly even if they don't go the extra mile. So get the right conductor and things will be great, get the wrong one and it can be a chore to upgrade. The one consolation is that the conductors change multiple times per trip. So if the first crew is a problem, wait for the change and try again.