I also thought it was stupid the way they just sort of dropped him off the face of the Earth like that. ASP couldn't have thought of anything reasonable to do with that? I mean heck yeah I was happy he was gone and made way for Lorelai and Luke but come on...
What I hated the most about him was how he often chose his job or working over Lorelai. He used business everwhere he went with Lorelai. Their first date was all about where he usually goes for business and that was very uncomfortable. He wasn't willing to do ANYTHING to interact with other people or to loosen up. He was on the cell phone pretty much RIGHT after he had sex with Lorelai... how romantic.

When he visted Stars Hollow all her cared about was translating to business men about insurance... Lorelai even had to be Luke and yell at him to get off the phone.

Then of course I didn't even have to WONDER why Lorelai never went to seek comfort with Jason in "The Incredible Shrinking Lorelais". Because all he would've concerned about was WHY her grandmother doesn't like him and wine about the antique book. To top it all off Jason pulls the lawsuit against her father even when she firmly states she can't be with him and begs him not to.

All he cared about at that point was him and his business. I understand he just lost his entire business and her father had everything to do with it BUT he could always rebuild his business and start over. He could always find another insurance company to take part in... ANYTHING if he really cared about Lorelai enough. But he didn't and wouldn't.

With this said, now I really don't care what happened to him. He could've gotten hit by that bus that missed Christopher for all I care. As long as he's gone and never ever coming back.