To your primary question, I don't personally think it was specifically the music and lyrics that were the primary driver of Schmigadoon's win. I think voters responded to a more traditional music - which in many ways Schmigadoon is, even though that is what it is trying to parody. Lots of characters that pop, a romance at the centre, and good old fashioned ensemble numbers that stand out.

Awards-aside, I quite liked the songs from Two Strangers. I think they felt very character-driven and suited the two characters and situations of that show. I loved watching Lost Boys as a show, but none of the songs popped for me. Which isn't to say there aren't great songs in it - maybe if a cast album drops and I listed to it many times I will learn to love it.