It's so striking to me that Lorelai has no opinion about the fact Luke kicked Jess out because he prioritized work and independence over high school... since that is precisely what Lorelai did herself? She ALSO dropped out of high school right before reaching the finish line, despite being smart enough to graduate. She obviously managed to build an amazing life for herself anyway. She never once voices regret over dropping out. It was the right choice for her!
So the fact Luke judges Jess so harshly and kicks him out without hesitation over making the SAME CHOICE Lorelai made for herself? Yeah. If I were Lorelai, I'd have some opinions on that. It's weird that she doesn't. It's another example of Lorelai seeing similarities between herself and Jess... yet sincerely believing that he did not need or deserve the kind of loving support she so readily received as an 18yo dropout.