Please tell me if I am I crazy for wanting to do this or if it is even practical?

In November I have to travel WAS-NRO for a quick family trip. This requires a regional train which usually costs about $160 in coach after discounts. The $160 fare results in a 320 or so AGR points at 2 points per $1. Now were I to book a multi segment ticket on the same train number I would be able to get a lot more points at AGR gives at least 50 points per segment. I would get about 600-700 points for the round trip. Instead of booking WAS-NRO I would book WAS-BAL-WIL-PHL-TRE-NYC-NRO or some combination all on the same train number. Would I be able to get all of my boarding passes in Washington from the machine? Would the conductor collect all of the passes at once?

Another way of doing it would be to use every station on the route, however this would be more stops then the website will allow. If I were to book one ticket WAS-PHL with all intermediate stops and one PHL-NRO with all intermediate stops would I have to pick up my PHL-NRO boarding passes in PHL?

If anyone has any thoughts, ideas or experiences with this please do let me know. I spoke with AGR CS and they told me that it would be legal.

Thanks,
GWU