As much as my initial like for Jed has faded away, I can't fault him for being excited about landing a contract to write jingles for a dog food company. It's steady income, and even if it's not the ultimate dream job, he is making money with music. It was probably the first time he actually made money with his music. I think it was his way of saying that it's not all just bars and stuff, it's a legitimate income.
Having said that: girl, when HIS family and YOUR family are doubtful and skeptical, walk away. Seriously. If you have to work THAT hard and feel THAT bad after the visit with your family, he's not the one.
I feel like, as with Luke, Hannah lasered in on Jed. And she didn't want to let that go. So she was surprised by her feelings for Tyler. When her mom asked if she could see herself being engaged to Tyler, it was a genuine reaction of joy. But she had already made up her end-game in her head, and didn't want to/didn't know that she could change that.