I hope we do see more of the Gilmores. I would like to see Rory given a chance to grow and make better choices, and I would LOVE to see Luke and Lorelai as grandparents.
As for which guy she should have chosen, I'm torn between Jess and Logan. I feel like Jess is Rory's intellectual equal and would have made a very good life partner, but Logan (pre non-exclusive relationship arrangement) grew on me and seemed to genuinely adore Rory in the latter seasons of the original series. I think they could have had a loving marriage if she would have said yes when he proposed. I also think they would have been able to work out a way for her to achieve her career goals. Jess would possibly have been even more supportive in that area, but I think their relationship might have been slightly less harmonious than one with Logan. Jess and Rory both seem prone to moments of intense emotion, and Logan seems to be a little more laid back. Dean, IMO, is horrid - at least as played by Jared. He's whiny, clingy, easily and excessively angered, and very controlling. I am so glad she did not end up with him, and I hated the storyline of them reuniting while he was married. That has to be one of the worst decisions she ever made and I'm disappointed she seems to have not learned from that particular mistake. If the show continues, I think I'd ultimately love to see Rory end up with Jess. He still seems to be very much in love with her, and, unfortunately, I now think the time for Rory and Logan has passed. And then there's always the option of not ending up with anyone.