Outlaws of Love:
I think it's a song Jon wrote somewhere between 1989 and 1991. I'm with you Dominik, that the first verse fits his situation with Dorothea at that time perfectly.
But I think that the demo happened with the band for Keep The Faith. Although the song itself would fit into the 80s, the band's play doesn't.
The muffled guitar riff sounds a bit like the beginning of I Believe where Richie does some kind of muffled slide, too, before he starts the dirty riff.
The line "These days you're two paychecks away" was used again in Hey God. So I think it's not too far fetched to say it's been worked on and recorded during KTF but it didn't make the record and while writing for These Days that specific line stayed in mind and was used again.