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Indeed the song was about Conway and Lysette.
[possible spoilers coming up!!]
It's all very subtle, so it can be hard to completely piece it together, even after a couple play-throughs. Conway didn't really leave Lysette to pursue a dream. At first, Lysette was married to Ira. Conway and Ira were supposed to do a roofing job, but Conway was too drunk and hungover to do it, so Ira and Lysette's son, Charlie, had to go in Conway's place. Charlie ended up dying after falling off the roof, and so Conway carried that guilt and could never bring himself to be with Lysette even after Ira died. Charlie's death is yet another example of that overarching theme: a debt that can't be repaid.
In Act III: Where The Strangers Come From, when Conway is inspecting the truck, you get something alone these lines:
Conway and Lysette met in a bar after church on a Sunday. They soon became lovers. It was the last year of high school. Conway's grade was bad and he didn't want to go to college anyway; while Lys had good grade and was going to college. So Conway went to another state for a job; while Lys went to college for a degree; they didn't hear from each other for many years.
Many years went by, as Conway switched between jobs and states. He finally got this roofing job from a man named Ira. After a few jobs, Ira invited Conway to his farm to see his wife and son; and it was then Conway and Lys reunited (but not really) with each other. Conway and Lys shut up about it though; the script says "as Conway always has".
We don't know when they came clear to Ira, or maybe they never did.
But as for back when they were younger, I tend to believe that Conway didn't think he was good enough for her. It wasn't that he had a dream; I don't think he ever really had a dream, other than perhaps hoping to make himself a better person who might then be deserving of someone like Lysette. I think he's always been fairly meandering and lost, purposeless.
As for "It's too late to love you," she sang that when she had already married Ira ("It's too late, I've made my vow"), thought the exact point when that happened, I'm not sure. It could have been after Ira hired Conway, which stirred up old memories for her.
I couldn't help but smile when I saw that phrase the second time and knew what it referred to.
It's really beautiful how everything fits together and even the smallest things are referenced somewhere else if you pay attention. This game is really something else.