Sometimes the outbound trains don't charge, but coming inbound from the more distant stations costs more.
They do it because it takes too long to have each person stop and pay.

At some of the stops, the rear door opens for people who have passes to just hold their pass up as they board. There are signs explaining this in the stations that do it.

There is no T etiquette.

I don't know about the student cards.

Yes you can. New York Penn Station is the Long Island Railroad Station. If you arrive on Amtrak you go down stairs and follow the signs to the Long Island Railroad Station. If you ride Metro North and arrive at Grand Central Terminal and take the subway to New York Penn Station when you get off the subway you will be on the Long Island Station level.

Is there anyway to get my Long Island Railroad tickets faster?

I ordered two tickets for this weekend thinking that i could just print them out after i ordered them and that would be that; but after i placed my order, i found out that the tickets would be mailed to be and i would receive them in 5-7 business days. The problem with that is that 5-7 business days would be between next Monday and Wednesday when i need the tickets for Saturday. I live in upstate New York and have no way of being able to pick up the tickets in person. Is there anyway to get my tickets to me faster?