Coming from another huge TRS fan, I have to somewhat disagree with your song choice for a new listener. I'd go more with Cross My Heart, TV Family, Around The Clock, Goodbye Waves and Driveways, You Gotta Believe and of course pretty much anything from Do You Feel. I almost despise Brat Pack haha.
Edit: oh but I HIGHLY agree the end is the best, most intense moment. I literally look forward to it each show. You get chills.
if i was trying to get someone into TRS, personally I would probably not play anything from calender days (maybe cross my heart or this is me, but doubtful), and very few from hello, good friend. I guess it depends on what style of music that person normally listens to really.. but I'd probably split a cd-r (yeah, a mix cd, thats how i do, haha) up between Do You Feel, and Of Men and Angels, maybe 1-2 tracks of Hello, Good Friend, maybe 1 from Calender Days.
I think it solely depends on if they listen to more indie music normally, then go for his earlier stuff, or if they listen to more pop/rock type stuff, go for his most recent.
I'd recommend This is me, treasures, show me everything you got, do you feel, all i have, high life scenery, a song is not a business plan, colors, so, in this hour, something to live for, walls, pull myself together, i need a break, hey, lights.
that's just me. . i feel, once they like the newer stuff, it's easier for them to accept some of his older stuff that seems a lot more indie/stripped down and has all his "ba ba ba"s from calender days, and "yelling" from hello, good friend.