Lyric discussion by selfishstars 

I think it's actually about being realistic when it comes to relationships. It doesn't matter how much you love someone or how compatible are you, you're always going to encounter hardships in your relationship. You can't just sit by and expect that your relationship is going to be perfect, you need to put in the time and effort every day to make your relationship better and keep it going strong--working out your problems, improving your communication, listening to each other, putting the effort into making the other person feel special and not neglecting them or taking them forgranted. If you expect that everything in your relationship is going to automatically be perfect, you're expecting that you're going to "win the lottery", and the chances of you finding a relationship like that are slim to non-existent. If you're disillusioned enough to believe that it's going to happen, chances are you wont put in the effort to MAKE your relationship good.

Saying you'd "rather be working for a pay check" is saying that you care about and want to be with this person so much that you're willing to put in the work to make sure you have a strong, healthy, and happy relationship.

He's not saying he's settling for her, he's saying she's worth any effort it might take to make things work between them.

Take the entire verse into consideration, "So if you want to be with me, With these things there's no telling, We'll just have to wait and see." It's like saying, if you want to be with me, there's no guarantee that everything is going to be perfect, but instead of just expecting it to be, I'm willing to work to make it as good as I can.

An error occured.