The rule that you can't slit up a ticket into multiple segments reads as follows:
Except as provided in this Section, Members who provide their Membership Number at the time of ticket purchase will earn 2 Points for every $1 spent on Amtrak travel, a minimum of 100 points for each trip. (The definition of a trip is the entirety of a member's travel in a given day, on the same train number.)


So, if I am on an overnight train and i split the segments up so each ticket starts on a different date I should get multiple points.

For example lets say I ride the LSL (Train #49) from SYR to SOB. I leave on Jan1 but arrive on Jan2. If i split it up into two segments SYR-CLE and CLE-SOB I have one ticket for Jan1 and one for Jan2.