I'm digging into another old track, based on a recent Doug episode.
So, this song was originally written FOR Tim McGraw. He didn't think it was special enough so he didn't buy it. "It wasn't a hit", as Doug put it. So Scott kept it and was really excited about it. That's why he booked that late night appearance to perform the song, even though there was no release date, no availability, nothing to promote.
Doug questioned that a bit, like "who does that?" but he also said that was one of the qualities he admired about Scott. The music excited him and he wanted the fans to hear it even though it would be years before it was available.
He said, it wasn't the only time that Scott pulled something like this off. The Leno "Have Yourself a Merry Christmas" was also in this vein, though it was Xmas time when he did that. But again, the Xmas album wouldn't come out for 2 more years.
Watching these videos, it seems like Doug is well aware of the "business" mistakes that were made over the years - and there were plenty - but many times, as he states, it was difficult to convince Scott not to do something. He regularly refers to him as "the boss" and they were following the boss' orders.