https://screenrant.com/gilmore-girls...nships-ranked/
'The central conflict at the heart of Gilmore Girls, beyond the generational family feud, was the push and pull between the upper and lower class structures that the Gilmore family inhabited. Richard and Emily represented the wealth that Lorelai deliberately raised Rory away from. But in the end, Rory found herself drifting away from the hardworking life, taking up with the human embodiment of privilege in Logan Huntzberger.
From day one, these two brought out the worst in each other, and it only became apparent over time. From repeated instances of cheating and public humiliation, to encouraging Rory to steal a yacht and drop out of Yale, and all the way to the disappointing affair storyline in the revival series, Logan made Rory an almost completely unlikable person.'
If I recall he didn't encourage her to steal the boat, but certainly enabled her. But I agree with the rest.